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- [00:00]
A
What if the software that every rookie landlord on Facebook keeps telling you to use is quietly the wrong one for your first rental?
- [00:09]
B
Or maybe you've been saving for a year to buy your first short term rental and then your city passes an ordinance that kills half of your nights overnight. Is this short term rental even worth it in 2026?
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A
And for anyone watching right now thinking there's no way in without capital, what if wholesaling actually might be the doorway, but only if you do it the right way on day one? We're answering all three today on Rookie Reply. This is the Real Estate Rookie Podcast. I'm Ashley Kerr.
- [00:42]
B
And I'm Tony J. Robinson. With that, let's get into our first question for the day. So question one, which comes from the BiggerPockets forum, says, I'm curious what you all use as property management software to screen tenants, create applications for tenants to apply, create leases, list of properties for rent, maintenance, et cetera, et cetera. A do it yourself program that is landlord friendly to a beginner landlord. Right now I'm using a Vail and I'm not loving it as I cannot upload my own rental application. What do you all use for your properties? So Ash, our resident long term rental property manager, Queen, you've used a lot of different softwares, right? So maybe just first just give us all the different ones you've used and then tell us what you're using today and why.
- [01:22]
A
Yeah, so I've used Rent Ready, I've used build DM, I've used AppFolio, and I've used Turbo Tenant. So I have not used a VAL that was talked about in the question. So I really can't give any kind of opinion or preference on that. But I will say there are categories of how many units you have as to which short term rent or long term rental property management software you should select. So when I was using Appfolio and Buildium I had at least 40 units. Plus they have a minimum fee that you have to pay no matter how many units you have. So if you have one unit, you don't want to pay AppFolio's $200 minimum. They're going to charge you every single month because that could be all of your cash flow. So there are these superior property management software that just has more bells and whistles. Ultimately most of them do the same thing. They have tenant screening, they collect rent online, they have messaging capabilities. So some of the ones, if you have like 50 units or less Rent ready Turbo Tenant, I'm pretty sure A VAL is kind of in that category of property management software is to you don't have a ton of units. What I would look at is do demos and look at the user interface because I do think that is really important as to how you interact with the software if you're actually going to enjoy using it. Because if you don't like logging into it and you get frustrated and you can't figure things out and you don't like the way it's viewed in the dashboard looks, you're not even going to implement it or use all the things it has to offer anyways. So do a demo on each of the different softwares that you're interested in looking at and the next thing is compare their capabilities. So Turbo Tenant, for example, that's what I use. And they have a lease auditor. So you will upload your own lease agreement and you will tell them what state you are in and it will go through and do an audit of your lease agreement to make sure that it complies with all New York State laws and rules and regulations will also give you recommendations of maybe things you should add in there. So, you know, I, I don't know of any other software that has that right now. Maybe some of the bigger ones that I don't look at anymore. But I really like that feature of Turbo Tenant. But so I think like also look what you want to get out of property management software. So is it the ease of the screening process? Is it just rent collection? And then also look at pricing too? You don't want to kill yourself on pricing if you only have a couple properties and you just need the basic features of the property management software too.
- [04:16]
B
Ash, one last question. How, how painful is it to switch from one PMS to the next? Like let's say that someone tries out one of these ones and they're like, I don't really know if I want to keep this one. I just want to jump to some, something else. Having gone through that yourself, is, is, is it somewhat seamless to move or is it really like, man, there's a lot of switching costs.
- [04:36]
A
When I did it myself, yes, super, super painful when I did it. I don't, this is probably five years ago, six years ago, and moving it all over, you would have to download every document, every receipt, everything that you had in there, move it over to the new one. So one recommendation I do have is I do keep double records. And yes, this is more work. But if you ever do switch software, even if you're using QuickBooks or things like that. I still do this even for bookkeeping is I'm saving in Google Drive a receipt, the lease agreements, any documents for that property for that tenant that I'm also uploading it so that I don't have to go in and manually down download everything right now. A lot of property management software has help with onboarding. So they will help you go through the onboarding process. This should be free, whatever one you're looking at. If they try and charge you, maybe you should be looking at another software. But do an onboarding call for them to walk you through that process and how do it. The second time I did it, I actually hired a virtual assistant at $8 an hour. I made a loom video saying here's one tenant, here's the information I want you to get from the property management software and here's how I want you to put it into the new property management software. And they went through and did it all for $8 an hour. I don't remember how much it ended up costing me, but not a lot of money at all to be able to move data from one to the other.
- [06:09]
B
Yeah. And honestly you could use something like, like Claude today to probably automate that for you now. Yeah.
- [06:16]
A
Okay, so we have to take a short break but you may think picking a property management software is the hard part, but maybe it's you're finally ready to buy your first short term rental next month and your city just rolls out new short term rental rules that basically are going to wipe out half of your projected income. So let's talk about short term rental investing. Is even still a strategy that will work in 2026? We're going to break that down right after a word from our show sponsors. When you buy your first rental property, there's usually a moment right before you pull the trigger where your brain starts spiraling a little. What if I'm making a mistake? What if I can't figure this out? What if this whole thing becomes way more complicated than I expected? Honestly, building any business for feels like that at first. And for a lot of investors, that next step is creating a brand, a website or even a business around what they're building. And I've learned this myself. Whether it's real estate, building a brand, launching a side business, or creating something online, the hardest part is usually just getting started before you feel fully ready. As a consumer, I use Shopify powered stores all the time. Chances are you do too. Some of the brands I buy from regularly run on Shopify. And you probably wouldn't even know it because everything just works. The checkout is smooth, the experience is easy, and that's exactly what you want if you're building a business and trying to earn customers trust. That's why Shopify makes so much sense. Shopify is the commerce platform behind millions of businesses around the world and 10% of all e commerce in the US from brands just getting started to household names. You can build a professional online store with ready to use templates that actually look good even if you're not tech sampling savvy. Shopify also has AI tools that help write product descriptions, page headlines, and even improve product photography. And instead of juggling five different platforms, Shopify puts everything in one place, from payments to inventory to analytics. Plus, Shopify helps you market your business with easy email and social media campaigns so you can actually reach customers. It's time to turn those what ifs into With Shopify today. Sign up for your $1 per month trial today at shopify.com Rookie go to shopify.com Rookie that's shopify.com Rookie when you're
- [08:38]
C
just getting started in real estate, it feels like every dollar has a job. Down payment, reserves, repairs, and then summer comes and you're like can I afford to take that trip or should my money stay in the deal? That was me recently. I didn't want to guess anymore though. I wanted to know exactly where I stood before decision. Monarch is the personal finance app that tracks everything accounts, investments, savings goals and spending. Get your first year of Monarch Core for half off just $50 with promo code Rookie. The first time I used it, I realized my savings rate had quietly dropped while my day to day spending crept up a little bit. Nothing dramatic, but it was enough to slow down my next deal. Now Monarch runs in the background. The weekly AI recap flags changes and I can actually see where my money's going and if I'm still on track. It's kind of like having a financial advisor in your pocket, especially when you're trying to balance life and investing. You can use code rookie@monarch.com to get your first year of Monarch Core Half Off. At just $50. That's 50% off your first year at monarch.com with code Rookie you just realized
- [09:48]
D
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- [10:55]
A
Okay, welcome back. Our second question today says I'm a beginner investor looking to get started with short term rentals. But I've been following the news and it seems like many cities are tightening regulations, issuing stricter permits, and enforcing occupancy rules. I'm trying to understand whether short term rentals are still a good strategy in 2026. Given these changes, any insights, personal experiences or advice would be greatly appreciated. I want to make sure I start on the right foot without running into unexpected legal or financial issues. So Tony, I took the first question. This one's all you.
- [11:36]
B
Yeah, so I it's a great question and I know a lot of people have questions about the regulatory landscape for short term rentals, but here's what I'll say, guys, is that the, the presence of regulations in an industry is not the end of that industry. Right? Like if you think about every other major industry that exists in the United States, there's typically some level of regulation within that industry. I think what, what makes short term rentals a little bit more jarring is the fact that, you know, there weren't a ton of regulations because short term rentals just weren't all that popular. And as they exploded in popularity, we just saw so many cities reacting to to try and keep up with the pace of short term rentals in their cities and their counties. So the mere presence of regulations is not a bad thing. Now that said, I think that there's, there's two different ways that you can approach regulations as a short term rental operator. The first way is to choose cities that are economically dependent on short term rentals. And then the second way is to choose cities where you have multiple exit strategies. Right now I'll break down both of those for the first way, choosing cities that are economically Dependent on, on short term rentals. Think about a comparison between a city like New York City and a city like Destin, Florida. New York City effectively banned short term rentals a couple of summers ago. And they did that because New York has zero economic incentive to protect short term rentals and the revenue that they generate. When you think about New York City and you think about all of the different industries that exist, they have everything. They have multiple, you know, professional sports teams, they have Wall street, that business headquarters, they have, you know, like, like literally every potential industry exists with some capacity inside of New York City. So for them, the little revenue that that short term rentals generates is like a drop in the bucket. You know, maybe not even a drop in the bucket. Right. Whatever is smaller than a drop in the bucket. That's how New York City viewed short term rentals. So of course they had no, no issues in, in banning Airbnbs. Now if you take a market like Destin, Florida, it is almost the exact opposite of New York City. There, there are no business headquarters, there's no major international airport there, there are no universities there, there are no major medical centers, there are no professional sports teams. There's no, like, there's nothing there except for people coming in, spending a few nights at short term rentals. Right. Spending money in the local economy and then going back home. So for a market like Destin, that is where travel and tourism is truly the backbone of that economy, they actually have a strong economic incentive to protect short term rentals. Okay, so that's the first approach, is to find cities where maybe there's a smaller permanent resident population. There's no, you know, there's low diversity of industries there. And where travel and tourism is truly the backbone of that, that local economy, that's one way to reduce regulatory risk. The other way to reduce regulatory risk is to go into a city where you've got multiple exit strategies. There are some folks I work with in, within our coaching program who, who bought in, in Pittsburgh and Pittsburgh might not, you know, at the surface level, seem like a place that's a great location to go buy a short term rental. But you know, when you look at the data, it actually is pretty strong. However, Pittsburgh also has a really large permanent resident population. Pittsburgh has, you know, all, you know, a lot of the things we talked about in New York City. So the, the regulatory risk in Pittsburgh is inherently higher than a place like Destin. So as we're working with those folks, well then the question becomes if, if we can't short term in Pittsburgh say regulations change. Can we midterm profitably? Right. Can we switch to 30 day stays or more and still be profitable? Could we, in a worst case scenario long term rent this thing and at least break even for us? So, so that's kind of like the cascading way that we look at it is option 1 or option A would be high economic dependence on short term rentals. Or then option B would be, hey, let's get multiple exit strategies.
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A
I think that goes with all strategies, to be honest, is to like we've seen a lot of our friends have midterm rentals and have to pivot to long term rentals because short term rentals weren't allowed in that market and the traveling nurses weren't there anymore as much as they were and they actually had to go to long term rentals or sell their property. So I think what you said is really important, being able to pivot and make sure the property has those exit strategies for any strategy that you buy it for.
- [16:23]
B
All right, guys, we're going to take one quick break, but while we're gone, if you haven't yet subscribed to the real estate rookie YouTube channel, you can find us at Real Estate Rookie and you can see mine and Ashley's smiling faces. And last, if you want to be a guest on the Real Estate Rookie podcast, head over to biggerpockets.com guest and get your application in. And we'd love to feature your story to inspire the next generation of rookie investors. But we'll be right back after a quick word from our show sponsors.
- [16:50]
C
Everybody has a space that's sitting there quietly, costing them money instead of making it a guest room holding random storage and a treadmill that hasn't been used in months, a second home that only gets used a few weeks a year, or your primary home while you're traveling, just sitting there, fully capable, producing zero return while you're away. It's actually a great opportunity to list your space on Airbnb and let it start earning for you. And if you've ever considered listing your place but assumed it would be too much to manage, there's an easier way. Now, with Airbnb's co host network, you can hire a vetted local co host to handle the details for you. A co host can create your listing, manage reservations, handle guest communications, and even provide on site support, giving you experienced help to take care of your home and guests without having to manage every detail yourself. So whether your space is empty on weekends, during certain seasons or most of the year. It doesn't have to sit idle. It can start producing extra income. It's a practical way to make more of the space you already have. Nice when something around the house finally starts contributing, find a co host@airbnb.com host
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E
okay, we're going to shift gears for a minute to cover something important, especially for new landlords. The shows often talk about getting stuck doing everything ourselves and the cost of sweat equity. The key question is simple. Is my time better spent elsewhere? I use a tool that cuts down on a lot of landlord hassles and the wild part is it's just $12 a month. It handles ren rental screenings, rent collection, maintenance requests and accounting all in one platform via a mobile app or desktop. It saves me time in tenant communication and keeps me organized for tax season. It's called RentReady and you can sign up for a six month plan for just $1 with promo code BP2025. Pro users get it for free because we believe in it. Just sign in through your Pro account to get started. RentReady helps ensure on time rent with auto reminders, keeps communication professional, and lets you post listings to multiple sites. Check it out@rentready.com BiggerPockets that's rent R E D I.com BiggerPockets tax season reminder
- [18:57]
C
for all the real estate investors listening if you own rental properties, short term rentals, commercial buildings, basically anything that's not your primary residence, you need to know about Cost Segregation. It's an IRS compliant strategy that lets you accelerate depreciation on your properties, which means you're paying less in taxes this year and keeping more cash in your pocket for your next deal. Cost Segregation guys is the go to firm having done over 12,000 of these studies with 500 million in total depreciation identified. Head to cost segregationguys.combp to get a free proposal and see your potential tax savings. There's a point where basically every investor realizes traditional financing stops scaling with you. At first it works. You qualify with your income, your job, your tax returns. But as you grow, that model starts to break. Now it's not really about your personal income, it's about the income from your properties. That's where DSCR lending comes in and it's why a lot of investors end up working with lenders like Host Financial. Host Financial qualifies deals based on property income, not personal income. So you're not dealing with W2s or tax returns or DTI constraints. And with 80 to 85% LTV, you can stay more Flexible as you scale. It's just a different framework, one that tends to align better with how investing actually works. If you're buying rentals, refinancing or growing your portfolio, go to host financial.com that's host financial.com and see what you qualify for.
- [20:31]
B
All right guys, welcome back. We are on to our final question. And this question says can anyone provide some advice on getting started with wholesaling and how to find good, reliable investors as well? Thank you in advance. All right, so wholesaling, what is it? We actually just interviewed Janelle Carlson. So if you look up Janelle Carl Carlson, you'll see an episode we did with her where she talked about finding off market deals and the bulk of her business is in wholesaling. But for our rookie investors who are not familiar with what wholesaling is, wholesaling is basically the actual of selling contracts in real estate. So you go out and you find a below market value property, you then get that property under contract and then you sell the rights of that contract to an end buyer, typically another investor who's going to flip it, burr it, whatever it may be. So, so that's what wholesaling is in a nutshell. And the reason that wholesaling is I think, attractive to a lot of newer investors is because you're not actually buying the property. So you don't have to come up with, you know, several hundred thousand dollars to buy the property. You are just getting the contract in place, which oftentimes costs nothing and then you're selling that contract at a profit, right? So it's like arbitraging real estate contracts basically. So, so that's what wholesaling is. Now how to get started. You know, you can do direct mail, right? There's a cost, you can put a billboard, you can run commercials, you can do a lot of, you know, pay per click. There's a lot of different ways to get started. But for me, if, if I was maybe looking for ways to get started with very little capital, I, I think the easiest way actually I'll give you two easy ways. I've seen people execute both of these. The, the first way is to network with real estate agents. I have a friend who runs a wholesaling business based out of California and Nevada and the majority of his deals comes from him just cold calling not, not homeowners, but agents and just telling these agents, hey, you're probably going to find some deals that maybe aren't, aren't a good fit for the mls. Let me be your first call. It's all he says. And he just, all day, he's just cold calling agents with that same spiel. And then every once in a while, one of them is going to say, hey, I remember this guy who called. Let me give him, give him a call. And that strategy is, is somewhat smart because the agents are cold calling homeowners all day, right? So you, you can call one agent who they themselves are cold calling a lot of homeowners, right? So your, your reach expands in a way and kind of multiplies in a way that would be hard if you're calling these homeowners yourself. And then I think the second way is just to partner with someone who's already wholesaling in your market, right? But like, if you can just go partner with someone and say, hey, I'll help source the deal, whether that's door knocking, you know, whatever you want to do. But. But then you can partner with someone else who, who can kind of show you the ropes of how to really scale that business up. But if I were brand new, I had limited capital, those would be the first two things that I focus on.
- [23:21]
A
Or look for somebody who's wholesaling but wants to get into your market and you be the boots on the ground for them. So, you know, like, you put out, put out in meetups or Facebook groups or whatever, get into the local wholesaling groups and, you know, put out there, I can be the boots on the ground. So even if it's not a wholesaler that's already doing it in your market, you could, you know, go to a wholesaler that already has a system, already has a process, has this business built, and help them bring it into your market. Also to the second piece of wholesaling is actually having you can get the deal locked up, but having somebody to actually buy the property. So you need to build also a buyer's list of, once you get these properties under contract, you need to have somebody to sell them to. You could go ahead and list them on the mls, but you also, if you can't close on this property when the contract comes due, then you need to make sure you have a way out. But most often the time, the way to wholesale is to sell it to an end buyer. There are people that do go in and what do they call it, Wholesaling, where they actually do buy a property, do nothing to it, and then list it on the MLS and sell it to whoever. But with, with wholesaling, you want to find buyers, and that's where going to the local Meetups, not working with other investors in the area. I went to a meetup in Buffalo before where there was a guy, he was doing his first wholesale deal and he had a clipboard and he said this is the property I got. He did his whole speech telling you all about it and he's like, if you're like interested in this deal or like any other deals I find in these areas, these are the areas I'm looking. You know, put your name and your email ends up. I knew exactly the house he had bought. It was right around the corner from my parents house actually. And I think my parents live in a great area. But this house was actually a meth house. Came to a big surprise to my parents and someone raided this house and neared them. But yeah, so it was a meth house and the people went to jail, whatever. And then I don't know, his foreclosed on something, whatever and it got into this wholesaler hands but he had no idea that it was actually a meth house house. And so, so be very careful because you need to do some remediation with that. You just can't. And that property is sat and sat and sat and it finally sold. But just you know, it's be, be careful and cautious of what you're getting into. If you do start wholesaling too is all you have to. All on that property he had to do is do a simple Google search of the address and all these news articles would come up saying that this was a house. But yeah, you want to find your buyers. And him going around that clip, he had a ton of names on there just at the small local meetup.
- [26:05]
B
Ashley, just, you know, just for my own knowledge. Are you aware what does remediation look like for a meth house? Like, like what do they even do?
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A
So that was my second Google after I confirmed that this was the meth house. That was my second one. But it's like fire and restoration companies can do the same thing. But you go in because the, the meth can like soak into the walls and the floor and everything. So like I don't remember exactly what it was. It was like something that you know, like it's recommended that it was like handled by somebody licensed with chemicals and things like that to remove it out like you would asbestos or something like that. But it could eventually be a lawsuit. You know, if you find out someone rented you a house that was used, you know, as a meth lab, then
- [26:56]
B
yeah, and you're raising your, your kids in this house, you know, well, learn. I learned something new every day in this podcast, so thank you for that.
- [27:04]
A
My parents lives near a mud house.
- [27:08]
B
That's the one takeaway from this episode.
- [27:10]
A
Well, thank you guys so much for listening to Real Estate Rookie. I'm Ashley, he's Tony. And if you guys have questions, you can reach out in the Bigger Pockets forums. Put your question in there. Most likely it will be answered by another investor before we even get to it on the show. But we love your guys questions, so please keep them coming. We'll see you guys next time.
- [27:30]
B
Hey rookies, if you're watching this, we want you to apply to be a guest on the Real Estate Rookie Podcast. That's right. Ashley and I are looking for amazing stories just like yours to be a part of our Real Estate Rookie Podcast. Now look, you don't need to be an expert. You don't need to have done thousands of deals. Even if you've done one deal, your story could help inspire the next listener
- [27:48]
A
as a rookie investor. Especially if you just got your first deal. It is all fresh in your minds and you are the best person to tell your story, give your experience on how you got it done to help someone else get their first deal.
- [28:01]
B
So head over to biggerpockets.com guest if you want to be a part of our show again, that's biggerpockets.com guest and we'd love to have you on. Every week, the Snap Judgment podcast drops you inside someone's biggest decision. The kind of decision you can only make once.
- [28:20]
A
With everything on the line, what do you believe?
- [28:23]
B
What do you want? And what would you risk to get it? Find out. Tap to listen now to Snap Judgment from KQED on Spotify.