AI Is Your New Business Partner

What if you had a business advisor on call at two in the morning when your tenant sends a threatening email, your insurance company denies a claim, or you need to know your rights before calling your attorney the next day? That advisor exists — and it's AI. In this episode of the Your Landlord Resource Podcast, Kevin and I get real about how we use artificial intelligence in our own rental property business, share the specific moments where it saved us time, money, and a lot of stress, and walk you through exactly how to use it yourself.

We cover two real stories that changed how we think about AI as a landlord tool. The first involves a domestic violence situation at our Sacramento 6-plex, where uploading our actual lease to ChatGPT at eleven o'clock at night gave us a detailed, clause-by-clause analysis of our options before we ever called our attorney — who couldn't add a single thing to what AI had already told us. The second involves a landlord in our community who used AI to find buried language in their insurance policy after a tree removal claim was denied, and recovered thousands of dollars as a result. Both stories come down to the same thing: having the right information at the right time changes everything.

Beyond the stories, we break down six practical categories where AI is making a real difference for self-managing landlords: document analysis, tenant communication, financial analysis, legal and compliance research, maintenance triage, and staying current on landlord-tenant law. We also walk through the third-story review of Kid 2's Idaho duplex lease — where AI caught confusing utility billing language, missing ESA acknowledgment, vaping and smoke remediation clauses, a plumbing liability gap, and a winter vacancy notification requirement that could have meant frozen pipes.

One of my favorite parts of this episode is the prompting segment, because it's where most people get stuck. The quality of what AI gives you is almost entirely determined by what you give it. We teach you the four-element prompt framework — Role, Context, Document, and Output — and share word-for-word example prompts you can use for lease analysis, insurance claim denials, contractor bids, and tenant communications. You'll be able to use these the same day you listen.

We also address the one thing that stops a lot of landlords from trusting AI: accuracy. AI can be wrong, and we don't sugarcoat that. We explain what hallucination means, why AI's knowledge has a cutoff date, and — most importantly — how to prompt AI specifically so it flags its own uncertainty instead of filling gaps with confident guesses. We even share the truth protocol we added to our own AI settings to keep answers grounded in verified, citable information. AI is not your attorney, your CPA, or your insurance professional. But used correctly, it will make every conversation you have with those professionals more informed, more efficient, and a lot less expensive.

WHAT YOU'LL LEARN IN THIS EPISODE

•      How Kevin and Stacie used AI on a domestic violence lease situation — and what a one-hour session revealed that matched their attorney and the California Apartment Association almost verbatim

•      How a landlord in their community used AI to recover thousands in a denied insurance tree-removal claim by finding buried policy language

•      The six practical categories where AI delivers real value for self-managing landlords: document analysis, tenant communication, financial analysis, legal research, maintenance triage, and staying current

•      How Stacie used Claude AI to evaluate a 34-unit building purchase using her actual financial profile — and what it revealed about her investment position

•      How AI reviewed Kid 2's Idaho duplex lease and caught seven critical gaps including ESA language, vaping clauses, plumbing liability transfer, utility billing confusion, and a winter vacancy notification requirement

•      The four-element prompt framework — Role, Context, Document, Output — and why vague questions get vague answers

•      Word-for-word example prompts you can use right now for lease analysis, insurance denials, contractor bids, and tenant communications

•      What AI hallucination means and why it matters for landlords asking legal or insurance questions

•      How to prompt AI to flag its own uncertainty instead of guessing — including four specific accuracy prompts

•      The truth protocol Stacie added to her AI settings — and how to set it up in ChatGPT and Claude

•      Why AI is a first-pass tool, not a final authority — and how to use it to show up to attorney and CPA meetings better prepared and more efficient

•      What to upload (and what never to upload) when using AI with sensitive rental documents

Episode 20 – The Nuts and Bolts of Residential Rental Property Insurance

EZ Landlord Forms – State-specific lease templates mentioned in the episode – https://www.ezlandlordforms.com

ChatGPT – https://chat.openai.com

Claude AI – https://claude.ai

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Transcript

Stacie 0:00

So here's the fun part. The next day when I called our attorney, I did not have to pay them to break all of this down for me. I was the one who presented all of my information and then asked the attorney if it was correct and if I had missed anything. Of course, he wanted to see the lease himself to verify all the information, but he was not able to add one more thing to consider or do. The information I had received from my one hour using AI gave me pretty much the gist of the situation and what my options were. The funny thing is, after I had done the work on ChatGPT, that night I emailed the legal support department that we get to use as a perk for being members of the California Apartment Association, and I included the lease and all the information that I had input into ChatGPT, and they came back three days later, and I kid you not, telling me almost verbatim to what AI had told me my options were.

Speaker 9 1:17

Welcome to Your Landlord Resource podcast. Many moons ago, when I started as a landlord, I was as green as it gets. I may have had my real estate license, but I lacked confidence and the hands-on experience needed when it came to dealing with tenants, leases, maintenance, and bookkeeping. After many failed attempts, fast-forward to today, Kevin and I have doubled our doors and created an organized, professionally operated rental property business. Want to go from overwhelmed to confident? If you're an ambitious landlord or maybe one in the making, join us as we provide strategies and teach actionable steps to help you reach your goals and the lifestyle you desire, all while building a streamlined and profitable rental property business. This is Your Landlord Resource Podcast.

Stacie 2:07

Hey, hey, landlords. Welcome back to the Your Landlord Resource podcast. I am Stacie Casella, and I'm here with my co-host, my husband, and my business partner, Kevin Kilroy.

Kevin 2:19

Hey there, everybody. Thanks for taking the time to listen to our podcast today.

Stacie 2:24

So what's new, Kev?

Kevin 2:26

Uh, let's see. We're getting ready to head back to Idaho in a few days here to visit kid number two and his girlfriend, and it's always a good time when we go back there.

Stacie 2:37

Yeah, we enjoy our time back there. I, I don't know about the rest of you, but when we visit, we like to take them out to dinner. And when we're working on our plans for our time out there, you know, we'll text him and ask him, "where do you want to go eat?" And kid two, he loves a good steak, right? So he's generally gonna suggest a good steakhouse that he wants to go to, and, that works well, 'cause we get to spoil him and give him a nice night out.

Kevin 3:04

Plus, your parents are joining us for this trip, so it's always nice for them to get away and visit one of the boys.

Stacie 3:10

Yeah. And my dad loves to garden, and kid two said that they have spent a couple of days cleaning up the yard, so Pop's not gonna freak out. So sometimes when we go, my dad will help him plant some veggies in his backyard. I think this time we're taking one day to go visit some wineries, so that should be fun. And kid two is planning a barbecue so that we can catch up with everyone that we know back there. But anyway, it's gonna be a nice time when we go. Um, let's get to our subject for today. So today we're talking about something that has genuinely changed the way that we run our rental property business. We're talking about artificial intelligence, also known as AI, and specifically how landlords like us and you can use AI as a real business tool. Not in some futuristic, robots are taking over kind of way. In a practical, right now, this is saving us time and money kind of way.

Kevin 4:17

And, you know, Stace, I'll be honest, I was skeptical at first. I'm, I'm not someone who jumps on every tech trend. But once I started using it and saw what it could actually do for specific landlord situations, I became a convert pretty quickly. And I think a lot of you are gonna feel the same way once you hear some of the examples we'll walk you through today.

Stacie 4:40

Yeah, exactly. I mean, I had the same feeling, right? You know, change is never easy, and I do think a lot of people are hesitant to start with AI because they're just not familiar with it. But it really has made a huge difference in how we run our rental property business, you know, in our personal lives as well. So here's how we're gonna structure this episode. We're gonna start with two real stories, situations we have personally been through or that landlords in our community have been through, where AI has made a measurable difference. Then we're gonna walk you through the categories of tasks where AI is genuinely useful for landlords. And we're gonna give you actual example prompts that you can use so you're not staring at a blank screen wondering what to type. And finally, we're gonna talk about something really important, and that's how to make sure that the answers that you get from AI are accurate and trustworthy because that is a legitimate concern and we want to address it head-on.

Kevin 5:47

This is gonna be one of those episodes you'll probably want to come back to. So maybe bookmark it or you could share it with a landlord friend who's still on the fence about this stuff. All right, let's get into it.

Stacie 6:01

Okay, the first thing I want to clarify is that this will not be a techy episode. We are not tech people. We have no idea how to code. We will not be discussing things like using AI to process your tenant screening or how to implement a chat box so that your tenants can learn how to handle a maintenance issue. Today, we are providing some very general information about how we have used AI, specifically ChatGPT and Claude to gather information quickly, which in turn helps us speed up and expedite our workflow. Okay, the point today is that using AI can save you a lot of time, and time is money, right? I have seen figures that suggest that when someone uses AI to research a topic, they can get results they need within minutes. Conversely, if they were to research that same topic on, say, Google, it could take them on average 30 to 45 minutes. So in essence, using AI can cut your screen time by 75%.

Kevin 7:07

That's a really interesting way to look at it. I, I mean, it makes sense, but I didn't even think about how it can cut down on screen time. I really was only thinking about the actual time you get back, but less screen time is a great way to look at it as well.

Stacie 7:22

Yeah, right. So you and I spend a lot of time in front of our computers, and I'll say that AI has really given me time back that I really need to put elsewhere, like for the kids or, you know, even taking care of things for my parents. All right I want to start with a situation that was genuinely stressful and complicated when it happened. We had a tenant who reached out saying that she was experiencing domestic violence in the unit and wanted out of her lease. And quick sideline here, we did a podcast all about it. We'll link it in the show notes for you. As a human being, obviously, your heart goes out to someone in that situation, but as a landlord, you also have another tenant still in the unit, the accused, and you have a lease that's been signed by both of them. What are your legal obligations? You know, what are your options? And I had questions I needed answered fast, and it was late at night.

Kevin 8:24

And I just want to do a quick sideline here that this domestic abuse was verbal, not physical, but it was domestic abuse nonetheless. And we got this information, it was actually the night we were flying home from kid one's wedding in Mexico, and you wanted to see if we could get some answers or at least get some information before you called our attorney the next day.

Stacie 8:48

Yeah. You guys, it's always good to have some basic understanding or knowledge about a scenario before calling your attorney. They charge so much money, and the more that you can find out before, the less you will hopefully have to pay for answers and guidance from them. Anyway, the tenant had texted us to let us know about what was going on. And I'm gonna be honest here, we had never had to deal with domestic abuse between tenants before. So we really only had general knowledge from our trainings on what their rights were. We really didn't know much about what our rights were. And I will say that for those of you who are not familiar with AI at all, it essentially is like Google. But when you ask your question or explain what information you are needing, the AI system you are using will retain that information and begin to learn about you and what your needs are. Within a conversation, AI retains everything that you share, so it can give you better answers as you go. And some platforms like ChatGPT or Claude have optional memory features that can carry information from one session to the next, which can be really helpful once you've set up your landlord profile. It's very specific if you ask your questions or formulate your requests with a lot of detail. Now, for this specific use, I had to introduce myself and give it some background information so that it could give me correct answers. For instance,, this was regarding our sixplex in Sacramento. I had to make sure that it knew that our property was a commercial property located in the city and county of Sacramento. That way, when it was looking for answers to my questions, it can give me correct knowledge if there is, say, a scenario where a commercial property owner might have different laws or ordinances that they have to follow. As opposed to, say, someone who owns a single-family home rental or a duplex which are not commercial rated. I also let them know that the property was owned by an LLC. Then I basically laid out the whole issue, that one tenant was allegedly being bullied by the other tenant, that the victim had provided proper proof to be able to give their 14-day notice, and I told them what the proof was. We included timelines, what had happened, and also included information about the remaining tenant. But what was so important and very impressive was that we uploaded the specific lease for these two tenants and asked, and I believe it was ChatGPT at the, in this instance. We asked AI to evaluate the lease to see where we had anything written in it that gave us the authority to evict the remaining tenant if it came down to us needing to get them out.

Kevin 11:49

Yeah. Now, that I thought was pretty cool. It was able to take our lease, compare it to California state law, and then apply our exact situation, and let us know that we had several clauses in our lease where... And here's the important thing to remember when dealing with domestic abuse we needed specific documentation in order to evict. Which was information we did not have. The victim only provided what they needed to get out of the lease, which for us was not enough proof to move forward with an eviction. But the long and short of it is, that in about an hour's time, Stacie had a lot of information about how domestic abuse laws work for rental property owners.

Stacie 12:38

Yeah. It was, it was pretty impressive. AI went through our lease clause by clause and identified the specific provisions that might apply to this situation. It also flagged that while we still had relevant language in our lease, enforcing it would require evidence that the outgoing tenant was not in a position to provide, and that information was critical. It didn't just tell me what I wanted to hear. It told me what was actually in the document and what the limitations were. And you guys, that's the kind of honest, specific analysis that's incredibly hard to get at 11:00 on a Tuesday night. So here's the fun part. The next day when I called our attorney, I did not have to pay them to break all of this down for me. I was the one who presented all of my information and then asked the attorney if it was correct and if I had missed anything. Of course, he wanted to see the lease himself to verify all the information, but he was not able to add one more thing to consider or do. The information I had received from my one hour using AI gave me pretty much the gist of the situation and what my options were. The funny thing is, after I had done the work on ChatGPT, that night I emailed the legal support department that we get to use as a perk for being members of the California Apartment Association, and I included the lease and all the information that I had input into ChatGPT, and they came back three days later, and I kid you not, telling me almost verbatim to what AI had told me my options were.

Kevin 14:34

And I think that was the key thing right there. You uploaded the actual lease document. You didn't ask a vague general question. You gave it something real to work with, and you got something real back. And we're gonna talk more about that when we get to the prompting section because the way you ask the question makes a huge difference in the answer you get. The second story I want to share is one we've heard from other landlords in our community, and it involves insurance, which is a topic a lot of landlords don't dig deeply enough into until something goes wrong, right? A landlord had a tree fall on their property during a storm. The insurance company agreed to cover the structural repairs but denied coverage for the tree removal itself. Now, let me tell you, tree removal after a storm is not cheap. We're talking potentially thousands of dollars. So in this case, the landlord pushed back. They uploaded their full insurance policy to an AI tool and asked it to find any language related to debris removal and storm damage. The AI software he used found specific coverage language buried in the policy that the adjuster had not applied, language that did support coverage for the removal. The landlord took that analysis back to the insurance company, cited the specific sections, and ultimately was entirely reimbursed.

Stacie 16:09

Yeah. That story gets me every time because it's a perfect example of information being the difference between having to pay a ton of money or not having to pay any money. That landlord didn't have a law degree. They didn't have a public adjuster on retainer. They had a laptop or computer and an AI tool and the willingness to actually dig into their policy. That's the level of access to information that we want every landlord in our community to have. Think about the two instances we mentioned here. Our situation using AI to research the domestic abuse issue that we had with one of our tenants likely saved us, I don't know, $500 or $1,000 in attorney's fees. Our lawyer charges $450 an hour. And yes, they reviewed our lease, but because I was able to present the issue plus what I felt were the next steps, I was able to ask them to just confirm that I was heading in the right direction. The knowledge I was able to obtain through AI allowed me to be in a position of having some background information, not just calling them with, "Here's the situation. What do I do now?" Because that could have been another hour or two of his time and mine going back and forth, likely over a period of a couple days. The other situation with the landlord and the insurance coverage for that fallen tree, his forethought to double-check his policy saved him thousands of dollars. So let that sink in. Two completely different scenarios, both landlords doing research for their rental properties, together saved thousands of dollars that would have come out of our reserves.

Kevin 17:59

Yeah. Well, like you said, time is money too. Maybe not the other guys with the insurance claim he had to fight for, but you saved hours of your own time using AI for the domestic abuse issue. And you know you can always use more time. All right, let's break down the categories where we think AI is genuinely useful for self-managing landlords. And we want to be clear here, this is not an exhaustive list. AI is a versatile tool, but these are the areas where we have seen the most practical value.

Stacie 18:36

Okay, so the first and maybe most powerful category is document analysis. And our two stories fall squarely in here. This means uploading real documents and asking AI to find specific things in them. So documents like your lease or your insurance policy, a vendor contract, a property management agreement, a demand letter from a tenant, a new city or state law that maybe you might be unsure on and you need to see if it applies to your rental property business or not. AI can read these documents and tell you what they say in plain English, what provisions apply to your situation, where the gaps are, and what questions you should be asking.

Kevin 19:22

What I love about this is that it puts you on equal footing with people who have more resources. You know, like a big property management company, they have staff who review these documents all the time, and they know what to look for. As a self-managing landlord, you might sign a lease you drafted years ago and never really looked at it again until something goes wrong. AI changes all that. It lets you get a thorough, specific read on your own documents whenever you need it. Here's a case in point. Kid Two, who owns a duplex in Boise, has both of his tenants renewing their leases. Now, originally, we helped him out with creating an Idaho state-specific lease on EZ Landlord Forms. And so when Stacie went back in to update the old lease for the current renewal, after she was done, she uploaded the, dare I say, 71-page lease into ChatGPT. She explained the situation that she was helping her son, who owns a duplex in Boise, Idaho, that she used a state-specific lease from EZ Landlord Forms and had made several additions to the lease so it covered Kid Two thoroughly. But then she asked, "Can you please read it over and let me know, where there might be any confusion or conflicting areas?" She also asked it to check for any mistakes or anything that was not included that should be for the best protection in the state of Idaho. And Stace, you want to tell them what it came back with? 'Cause I really found this fascinating.

Stacie 21:05

Yeah, sure. It was really cool and it, it caught a bunch of items. So much so that now I want to go over our lease that we use in Sacramento to make sure that these items are included. Okay, so Kid 2 charges a fee for utilities, much like we just started doing. The fee covers water, sewer, trash, recycling, and landscaping. But in the body of the lease, it notes that the landlord will bill the tenant separately for these utilities. Then later it states there's a flat fee for the utilities. The confusion is that is he billing for the use or just charging a reimbursement fee? Because if it's for the use, he would have to provide copies of the billing from each of those utility providers and show how it was divided up, which actually is a RUB system and that is best used on, you know, like really large apartment complexes, like 12 units or more. And Chat came back and suggested the wording to add to the lease to clarify both those statements. And it was something like, "Tenant shall pay landlord a flat monthly utility reimbursement of $100 for water, sewer, trash, recycling, and landscaping. This fee is considered additional rent and is due with the monthly rent. This fee is not based on actual utility usage." It also suggested to remove the confusing language included in the body, but unfortunately, with EZ Landlord Forms, you cannot make changes to their main body of the lease. You have to add in your own language in the, quote-unquote, "additional information sections," which is where you have the opportunity to write what you want. Anyway, I'll go through these pretty quickly, but some of the other changes were the body of the lease stated to change air filters as needed. Chat suggested putting in there a timeframe, so we added every 100 days or sooner if needed. Under the plumbing section, it suggested to add, "Tenant shall not flush wipes," and then in parentheses, "including products labeled flushable, feminine hygiene products, paper towels, grease, diapers, cat litter, or similar materials into the plumbing or sewer systems. Tenant shall be responsible for plumbing repairs or drain clearing caused by improper use."

Kevin 23:35

And that last sentence is key there. That transfers the responsibility to the tenant. They cannot come back and say they didn't know. And they cannot say it's Kid Two's responsibility to pay for the repairs.

Stacie 23:48

Yeah, exactly. It essentially transfers liability to that tenant so that when the plumber goes out to clear that clogged drain or toilet and they find wipes or whatever created the issue, kid Two can now pass the charge for that plumber onto the tenant. All right, let me tell you a couple more items chatGPT caught. This next one is important, and I'm not sure that our lease covers it completely, so I need to check that out. Now, Kid 2 has a no smoking policy. We do as well. No smoking anywhere in or on the property. If they want to smoke, they have to go out to the sidewalk or they have to leave altogether Vaping has become a big thing now, and it does not smell like cigarettes or cigars, right? So Chat suggested adding the following clause: "Tenant shall be responsible for costs associated with smoke remediation, odor removal, HVAC cleaning, fire department charges, fire-related damages caused by tenant negligence, unauthorized smoking, vaping, candles, grills, or misuse of appliances."

Kevin 25:02

I really like that one. Because not only smoke, but odors or damages from candles or those, you know, stinky plug-in room deodorizers too. It even goes so far as to say if you burn something in the oven that causes the unit to smell like smoke, you can go after them for reimbursement.

Stacie 25:23

Yeah, I mean, that's honestly, it's gonna be tough to prove that one, but bottom line, he's covered if he can prove it. So the next one I'm not gonna go into, but it was helpful. Under care, cleaning, and maintenance, it just said that they had to report issues of mold, leaks, appliances, HVAC, et cetera, within a reasonable timeframe. And Chat suggested to add within 24 hours of discovery. Because the term reasonable timeframe, you know, that's different for everyone. For leaks and mold, waiting a week or two can make a huge difference.

Kevin 26:03

Well, if the AC isn't working, sometimes just getting a repair person out there can take a few weeks. And if their reasonable timeframe is to wait until there's a heat wave, that tenant is screwed.

Stacie 26:15

Right. But tenants don't think like that, you know, not all. But most do not understand the hoops that we landlords have to jump through to get something repaired in a timely manner. Okay, two more things I want to talk about that AI found wrong with the lease. So Kid Two has a no pet policy, and it's not that he doesn't want pets, he just wants to approve them before they're secured. So the lease, which was shocking to me, it just stated, "No pets allowed." And ChatGPT came back and essentially said, you have to acknowledge ESAs, and then suggested adding this clause: "Pets are not allowed without landlord's prior written approval. This policy does not apply to legally required reasonable accommodations for assistance animals as required under applicable fair housing laws." Boom. Covered his butt in case someone decided to get testy about an ESA. Now, the last one that I want to share, and there were many more, but these are the most important ones. This last one is important for homes or units that are located in areas that get below freezing temps in the winter months. Because Boise, Idaho, can get some cold spells, AI suggested adding the following clause under the winter weather maintenance section. And here's what it says: "Tenant shall immediately notify landlord if the property will be vacant for more than seven consecutive days during winter or the following months, November through April." Now, this is so that should the tenants turn their heater off when they leave town a freeze warning comes through, Kid 2 can head over to the unit and turn on the heater to like fifty-five degrees so the pipes don't freeze.

Kevin 28:07

It's really all about communication, right? This is not something that we really need to worry about in our rentals in Sacramento. Our mountain homes, yes, if we left the water on for a rental, but it's not something we would have considered.

Stacie 28:22

Right. So you guys, those examples right there are some things that we have used AI to help us evaluate documents that we use in our rental property business. We don't have them create the whole lease. It's just like having an extra set of eyes with a ton of resources that can make our research so much more easier and efficient.

Kevin 28:43

Exactly. Those are some great examples of how you've used AI for our documents. So let's keep going. The second category is tenant communication, and this one is really underrated. When a tenant sends you an angry email at, I don't know, nine o'clock at night, your first instinct might be to fire back or to panic, and neither of those serves you well. What you actually need is a professional, neutral response that acknowledges the concern, states your obligations clearly, doesn't admit liability, and sets a clear next step. AI can draft that for you in about 30 seconds. You paste in the tenant's email, you tell AI what outcome you're looking to achieve, and you get a polished response that you can edit and then send.

Stacie 29:40

Yeah. The key word there is edit. You know, you're just using AI for a guide. You have to edit what it comes back with.

Kevin 29:49

Exactly. Again, the more you use the program, the more it learns about how you like to write. You can tell it you want a professional tone or a more relaxed, friendly tone for your emails. But I want to add to what Stacie just said. What you receive back from AI is not exactly what you want to send. Always verify what it gives you. Do not just cut and paste the information and send it out. We use AI a lot, and we'll find errors or changes we like to make, you know, depending on the situation.

Stacie 30:27

Exactly. You know, it, it's also great for things like lease violation notices, non-renewal letters, security deposit disposition letters. Any communication where the language matters and where saying the wrong thing could create legal exposure. You're not having AI write the final document. You're using it to get a solid first draft, and then you review it and you personalize it, and it's a huge time saver.

Kevin 30:56

Okay. The third category is financial analysis, and this is one I use pretty regularly. Whether I'm evaluating a potential new property purchase, trying to figure out if a rent increase is justified, or reviewing a contract bid to see if something looks off, AI here is a really useful thinking partner. You can share numbers, ask it to walk you through calculations, ask it to flag anything, that seems unusual, or ask it to help you think through a decision from multiple angles.

Stacie 31:31

I just used AI to evaluate the purchase of a potential property that I wanted to buy. A little bit out there, but it was a 34-unit building, and of course, I don't have the money for it, but I wanted to know what my options were, cause there were a lot of parts of this building that fit right into what we want, right? And all you hear online is, "Where there's a will, there's a way." So I thought I'd check it out. This time, I used Claude AI, and I uploaded the address, the seller's marketing package, and all of my information on what we own, how much cash I had, everything like that. And it came back with a bunch of questions. You know, it's patient. You can ask follow-up questions, ask it to explain its reasoning, ask it to recalculate with different assumptions, and it, it doesn't get frustrated if you don't understand something the first time. So for landlords who are building their financial literacy alongside of their portfolio, having this in your back pocket is really genuinely valuable. And it came back to me with several options. Now, only one of them was really doable, and unfortunately, the parameters were so tight, I doubt that it could work. You know, for that property, the way that it would work for me and the seller, I would need several hundred thousand dollars in reserves, and I, I just don't have that. Not yet anyway. So for now, I just keep looking. But let me tell you that, one, doing that evaluation really helped me understand what my financial situation and investment position is. And number two, now that I have entered all that information into the system, Claude now knows what my assets look like, what cash I have, and a really good idea of how I want to proceed. So that now all I have to do is upload a seller's marketing package and have Claude quickly evaluate it. It will then ask me some questions about my current goals and needs, and I can know fairly quickly if this property is something I want to move forward with or move away from.

Kevin 33:49

That's really interesting. Because your management needs are different depending on the location of the property, right? So for a property in Sacramento, Claude now knows to remove the cost of a property manager. But for something out of state, it will have to include a management fee in the financial analysis. Okay, so let's move on to our fourth way landlords can use AI to help with their rental property business, and that is legal and compliance research. And we want to be upfront here. We are not attorneys, and AI is not your attorney either, but AI is very good at helping you understand the landscape before you talk to an attorney or helping you figure out what questions to ask. Things like notice periods for your state, fair housing basics before you write a rental listing, what habitability standards apply to a specific repair issue, or what the eviction process looks like in your jurisdiction. You get a solid working understanding, that helps you have a much more productive conversation with the professionals you're paying.

Stacie 35:01

Right. The key is to always verify state and local specifics independently. And this is why I was specific and said Kid Two owned property in Boise, Idaho, not just Idaho. Laws change, cities sometimes have stricter rules than state law, and AI will often tell you this itself. It'll flag when something might vary by jurisdiction. So pay attention to those flags.

Kevin 35:28

Good point. Okay, the fifth thing you can use AI for is maintenance triage. Your tenant calls and says water is dripping from the ceiling after it rains. Is that urgent? What are the likely causes? Is this a tenant issue or a landlord issue? AI can help you think through the diagnosis before you call a contractor, which helps you have a smarter conversation and avoids being taken advantage of. You can also ask AI to review a contractor's estimate line by line and flag anything that seems vague, overpriced, or missing.

Stacie 36:05

Yep. Same thing with appliances that are not working properly. Upload the make and model number, 'cause we know you have that in your file now 'cause we told you to do that. Then tell it the issue, and it can give you an idea of what is wrong before you call your appliance repair person. This also allows you to be able to communicate better with them, and if they agree with the possible issue, they might be able to come to the job prepared with parts so that they can fix it right there and then. We've also used AI to build out maintenance schedules, like a seasonal checklist for each property type that makes sure that we're not missing anything. It, it's the kind of thing that would take a couple of hours for us to build from scratch, but it takes about 10 minutes with AI. Again, just using the ideas of what it comes back with because every property has its own individual needs for maintenance and also different needs depending on the time of year. All right, the sixth and final way that landlords can use AI to help with their rental property business is by learning and staying current with landlord-tenant laws. When a new piece of legislation gets passed and affects landlords, you can cut and paste that text right into AI and ask it for a plain English summary. When you encounter a legal term in your lease that you don't recognize, ask AI what it means and for examples on how it typically plays out. When you wanna understand a concept like depreciation recapture or 1031 exchange, AI can walk you through it at whatever level of detail that you want. It really is like having a very knowledgeable study partner on call all the time. Now, let me take a second and tell you how AI gathers their information. So AI has learned from a huge amount of text, websites, legal documents, books, all kinds of sources, but it's not browsing the internet live when it answers you. It's drawing on what it learned up to a certain date, which is why verifying current laws and regulations matters. Some of those sources are truthful, some not so reliable. So it's important that you take the time to verify the information that AI has provided and not just assume that it's 100% correct and truthful.

Kevin 38:29

Or that it applies to your exact situation. Sometimes AI will answer you based on what it already knows about you from previous conversations. So how you ask your questions, it makes a huge difference. And that, my friends, leads us right into the next segment, how to write your prompts so you get real answers.

Stacie 38:52

Okay, this is a section that I'm excited about because I think it's the thing that separates landlords who get a lot of value out of AI from landlords who will try it once, get a mediocre answer, and then give up. The quality of what AI gives you is almost entirely determined by the quality of what you give it. If you ask a vague question, you're gonna get a vague, generic answer. Ask a specific context-rich question, you're gonna get a very specific, actionable answer that applies to your situation personally.

Kevin 39:27

Absolutely right. Think of it like briefing someone who's very smart but who has zero context about your situation. They don't know where your rental is located, like the city and state. They don't know how your lease is written. They don't know anything about your tenant, and they don't know what outcome you're hoping for. The more you tell them upfront, the more useful their response is going to be.

Stacie 39:54

Yeah, exactly. So there's four elements that we suggest you build into every prompt you write, and those are role, context, document, and output. Let me say it again. Role, context, document, and output. And we're gonna walk you through each one. All right, so role. That means telling AI what kind of expert you want it to be for this question. So you're not just asking a general question into the void. You're saying, "Act as a landlord-tenant law specialist," or, "Act as an insurance policy analyst," or, "Act as an experienced rental property owner or property manager." Another one is, "Act as a financial advisor for real estate investors." That framing shapes the entire response that you're gonna get.

Kevin 40:51

Essentially, you want to figure out who you wish you could ask your question to and then tell AI, "Answer like that person, company, or type of professional." Context means giving the actual situation, not just a summary of it. Don't say, "I'm having a tenant issue." Say, "I am a self-managing landlord of a single family home or a duplex or a fiveplex in San Francisco, California. My tenant has not paid rent for thirty days. I sent them a three-day notice to pay or quit on the fifteenth. They responded with an email claiming the unit is uninhabitable. I have attached that email for your reference. If you have more information, you're going to want to include that. If not, ask, "What are the next steps I should take?" That level of context gets you a response that actually applies to your situation.

Stacie 41:52

Yeah, that step is so important. And I'll tell you honestly, it's one that it took me some time to learn. And I realize a lot of people don't wanna put personal information into AI, and for that last part, you don't need to. It can be more generalized. But with the next element, that personal information is hard to get around. So document means that you're going to upload the real file whenever possible. This is the one that makes the biggest difference for lease and insurance questions. Don't describe your lease. Give AI your lease. Don't paraphrase your insurance policy. Give AI your insurance policy. The analysis that you get from the actual document is in a completely different league from the general information that you get just from giving a description. When I mentioned earlier that I had uploaded the lease and ChatGPT found exactly where and what language was used to potentially evict that tenant, that is why you need to upload the document. Please do not upload any information that can get you in trouble. So don't upload rental applications that have Social Security numbers on them. Don't upload photos of children. Do not upload personal records that a tenant may share as evidence for something, like medical records to prove a disability or the need for an ESA, which honestly, those last ones, you can't even ask for them, but some tenants willingly then send them over as proof. If you're privacy-conscious, leases with tenant names and addresses should have that information redacted since those are personally identifiable. What you can do is upload a blank lease, the same exact lease that they would sign, and that would work just the same. Your own insurance policy or a marketing file for a property that's for sale, those are things that you can enter into AI and have them evaluated so the answer you receive is very specific.

Kevin 43:55

Yeah, I can see how new users might be hesitant to upload any documents, but boy, what a difference it makes in the response you get. And just a heads up, uploading documents sometimes requires a paid subscription on AI platforms, but it is absolutely worth it for everything we've talked about today. But just know the free versions can be more limited.

Stacie 44:20

Yeah, and it depends on which one you use. I have decent luck with both Claude and ChatGPT, but there's a limit on how much information you can get at one time. When you're using an unpaid account and start uploading documents and asking a bunch of questions, the system usually will time out and ask you to come back at a later time to continue. On a paid account, you have more options and usually an unlimited time to to chat back and forth with the platform. I will say that we started with ChatGPT and do have a paid account with them, but I do tend to prefer Claude and the way that it interacts with me. And I know this sounds crazy, but it seems more personable to me than ChatGPT. The way it responds appears to be more thoughtful and intuitive. Yet I don't have a paid account with them yet. So I don't know. Maybe when the ChatGPT account is ready to renew, I'll just, I'll switch over to Claude.

Kevin 45:17

Is Claude your new friend, Stace?

Stacie 45:21

You know, for some introverted people, I can see how these AI systems can appear a safe space to communicate with.

Kevin 45:29

Yeah. Well, that's all kinds of sad and scary. And certainly not what we are implying here today. Okay, moving on from documents as we kind of strayed from the main point there. The last element is output, which means tell it exactly what you want back. Do you want a list of relevant clauses? A yes or no answer with reasoning? Maybe a draft letter? A comparison of two options? Or it could be a step-by-step action plan. Whatever it is, be specific about the format, and AI will deliver it in that format.

Stacie 46:10

Yeah. This goes back to being as specific as possible. Often I'll just ask what my rights are or what steps to take in order to resolve an issue, and it'll come back and ask if I would like it to draft an email or create a checklist. Or like when I was asking about that 34-unit building I wanted to buy, I asked for all the different options on ways I could purchase that property, and it came back with about four that were doable. Okay, let me give you some actual example prompts that you can use. For a lease analysis situation, you can type something like this: "You are a landlord-tenant law specialist. I am a self-managing landlord in," and then put your city and state. I've uploaded my lease agreement. My tenant has stopped paying rent and is now claiming the unit is uninhabitable due to a plumbing issue I was not notified about until today. Review my lease and identify, one, what my obligations are regarding habitability and repair timelines. Two, whether rent withholding is addressed. And three, what my options are for proceeding with a non-payment notice. Flag any causes that could work against me. It's gonna take a minute to think about it, and then it will either come back with an answer or it will ask you questions to gather more information. Like it may ask you if you own a single-family home or a multifamily property to distinguish if there are any law differences based on the size of your rental. Because in California and in many states, five or more units in one building is generally classified as commercial. But check your local laws because that threshold can vary.

Kevin 48:01

That's a good point. Let me give you another prompt example. For an insurance claim denial, try this: "I have uploaded my landlord insurance policy. My insurer denied coverage for," and then describe the specific damage. Review the policy and identify, one, any language that could support a coverage argument, two, any exclusions that apply, and three, the exact page and section number of relevant clauses. Do not speculate. Only cite what is actually written in the document."

Stacie 48:40

Yeah. And again, the more information you give, the better. That insurance one is used very often. We had a listener text or email us a question about how to handle a situation that involved insurance coverage and their tenant, and we suggested they upload their policy into AI to see if there was anything that they were missing. That same prompt can be used when you're looking to renew your policies as well. Upload your old policy, and see where there might be gaps or lack of coverage that you just assume is there. Many of you do not have a specific insurance broker to call and go over the policy to make sure that you're covered the way you want. When you do your policies online, it's all on you to make sure that you get the coverage that you need, and that's where AI can really help you out. Just a little sideline here, we did do an episode all about the nuts and bolts of residential rental property insurance. It's episode 20. You can go check it out at yourlandlordresource.com/episode20. All right. Another common use for AI is to have it evaluate a contractor's bid, and you can ask it something like this: "I've uploaded a contractor estimate for a," and then put in the type of repair or work you're having done, on my rental property. Review each line item and flag, one, anything that seems unusually high based on standard repair costs. Two, any line items that are vague or undefined. Three, anything missing that is typically included in this type of repair. Tell me what questions I should ask before signing that document. This is a good one because sometimes disposal of trash is not included. Sometimes if the job goes over the timeline, they can charge you more if those delays are caused because of you. For example, the tile that you ordered did not come in on time or you ordered the wrong size appliances. And sometimes they write in a bonus for finishing early.

Kevin 50:49

And sometimes you are stuck with their subs. Like for us, when we did the remodel of our kitchen here many years ago, we wanted to use Stacie's cousin, who's an electrician, to add recessed lights to the living room adjacent to the kitchen, along with the kitchen remodel electrical work. Our contractor came back and said, "Use him for the other parts of the house that I'm not working on. I'll have my guys do all the work for the kitchen, which was what I was hired for." So sometimes that information is written in the bid. Here's a prompt for a tenant communication situation: I am a landlord of a single-family home or multifamily rental property located in, and then give the name of the city and state. My tenant sent me the attached email. Draft a professional factual response that, one, acknowledges their concern, two, states my legal obligations clearly, three, does not admit fault or liability, and four, sets a clear next step. Keep the tone firm but respectful.

Stacie 52:02

And that's important. If you're asking it to draft an email or a response for you, it's important to make sure that you note how you want the tone of what it is drafting to be. Is this a friendly reminder? Is it a firm and professional notice? Should the draft show any emotion? These are all perfectly fine to add in, and often if you forget, AI is gonna come back and ask you what tone of voice you'd like it to be written in.

Kevin 52:29

Yeah, that's another good point, because it's good to know that AI usually will ask you about the tone if you forget. All right, we are finally on our last segment for this episode, and we have to talk about this because it's the most important thing we're gonna say in this entire episode. AI can be wrong. Not just occasionally. It can sometimes be confidently, smoothly wrong. This is called hallucination in the AI world. And it means the tool presents inaccurate information as if it were fact.

Stacie 53:08

Yep. And for a landlord asking about state eviction law or insurance coverage, that's a real risk. But here's the thing, this risk is not unique to AI because you can get bad advice from a neighbor or a forum post or a real estate investor, a Facebook group, or even an outdated legal guide. The question is always: How do I verify what I'm being told? And the answer with AI is actually really actionable. The first thing to understand is that AI is not connected to live legal databases. Laws change. Notice period requirements change. Rent control rules expand. AI's knowledge has a cutoff date, and local rules are where it's most likely to have gaps. So for anything state or city-specific, like eviction timelines, required notice language, security deposit limits, treat AI's answer as a starting point and then verify it against your state's official landlord-tenant statutes or with an attorney. The second thing is to prompt AI specifically for accuracy. You can ask AI to be transparent about what it doesn't know. So here are some prompts that will get you a much more reliable and honest response. Try adding this to any document-based question. Only answer based on what is written in the document I uploaded. If the document does not address this question, say so explicitly rather than making an assumption. Or if you are uncertain about any part of your answer, flag it clearly and tell me what I should verify independently. For document analysis specifically cite the specific clause, section, or page number for every claim you make about this document. If you cannot pinpoint to a specific language that supports a claim, do not make the claim.

Kevin 55:14

And for any legal or regulatory question, you want to tell it, do not speculate. If the answer requires knowing local law or specific facts I have not provided, tell me what additional information you need before you can answer accurately.

Stacie 55:32

Yeah. So you guys, when you prompt this way, AI responds differently. It becomes more careful, and it flags its uncertainty. It tells you where to verify. It draws a clear line between what the document actually says and what it's inferring. And that's the version of AI you want working for you, not the one that fills in gaps with confident guesses. Now, and I'm not sure where I found it, likely somewhere on Instagram, but in whatever AI system you use, we use ChatGPT and Claude. Under your profile in the settings, there is some place to add instructions. So for ChatGPT, it's under settings, and then click personalization, and then go to custom instructions. In Claude, it's under settings, click general, and then go to personal instructions. Now, this navigation may shift a little as they update the platforms, but basically you're looking for settings and then personalization or custom instructions. Anyway, this is what I entered to help make sure that the system knows we have a truth protocol. Here's what I typed. "You are operating under the truth protocol system. Your rules are strict. Always tell the truth and use factual claims. Base answers on verified, credible, and current information. Cite sources clearly when making factual claims. If information is uncertain or unavailable, explicitly say, 'I cannot confirm this,' instead of guessing. Never invent data, events, people, studies, or quotes. Do not speculate or present interpretations without strong supporting evidence, and always identify when you're doing so. Failsafe check. Before every response, internally ask yourself, 'Is every statement I'm about to provide true, sourced, and transparent?' If the answer is no, revise it until it is yes. Prioritize accuracy over speed or creativity. Provide step-by-step reasoning for complex answers. Show calculations when giving numbers or statistics. Be transparent about limitations and confident levels in every response." Now again, somebody on social media put that out, and I copied and pasted it. I did not create that, so if you use it and you get incorrect information, don't come back at me. You can create whatever truth protocol you want.

Kevin 58:11

Well, I would say that's a really good start at making sure that the information AI provides to you is truthful and verifiable. And when AI provides a reference on where they got their answers from, read it, because it may be information that does not apply to you or just vaguely applies. You know, the broader principle is this: use AI as a first pass, not a final authority. It is an incredibly powerful tool for getting up to speed, identifying the right questions, finding language in documents, and drafting communications. What it is not is a replacement for an attorney, a CPA, or a licensed insurance professional when the stakes are high. The combination AI plus professional verification where it matters is where the real value is.

Stacie 59:09

Think of it as the difference between showing up to a meeting prepared versus showing up cold. Lawyers and CPAs have very high hourly rates, and the more you know going in, the more time you have to discuss your personal situation. You're not going to waste a lot of time and money being brought up to speed on information because you're already familiar with it, and AI helps you get prepared. But you still have to bring the professionals in when decisions have real legal or financial consequences. That's how we use it, and that's how we recommend you use it.

Kevin 59:45

All right, so let's bring this episode home. AI is not magic, and it is not a replacement for professionals you need in your corner. But it is a genuinely powerful tool that gives self-managing landlords access to a level of analysis and support that used to require either a big team or a lot of expensive professional time. Document review, tenant communications, financial analysis, legal research, maintenance triage, staying current on legislation, all of it is more accessible with AI in your toolkit.

Stacie 1:00:25

And the key to getting real value out of it is to use it intentionally. Upload your actual documents, give it real context, tell it what role to play and what output you want, and ask it to be transparent about what it doesn't know. And when you do those things, the answers that you're gonna get will be genuinely useful, not just a generic paragraph that could apply to anyone. All right, you guys, that is our show for today. Thank you so much for taking the time out of your busy schedule to listen to what we have to say about using AI when self-managing your rental properties. We are very grateful and very humbled to be able to share what we know to help you in your journey. Now, if you enjoyed this episode and got some helpful information out of it, would you mind helping us out by leaving a review? You know, we would really appreciate it. Even sharing the podcast with another landlord that you know, that would be great. If you want to hear more, follow or subscribe to the podcast so that each week the episodes are downloaded right to your podcast platform. And we'd love to stay in contact with you. If you have a question or you want to suggest a subject for a podcast, you can text us at (650) 489-4447, or email us at stacie@yourlandlordresource.com. That's Stacie with an I-E, or kevin@yourlandlordresource.com. We'll link those in the show notes as well. I think that's about it. Thanks again for tuning in, and until next time, you've got this landlords.