3 Cash-Flowing Real Estate Deals in 2025 (& Where We Found Them)

Ashley:
No matter what anyone else tells you, there are profitable real estate investments available on the market right now. You just need to know how to find them and how to implement the right business plan to maximize your returns. Depending on the property and the market, that might mean a short-term rental strategy or a long-term one. Today we’ll show you how to project expenses, revenue, and other key metrics for either strategy. Select the best one to achieve your goals and put yourself on the path to financial freedom. Hey everyone, it’s Ashley Kehr guest hosting the BiggerPockets Real Estate podcast for Dave Meyer. Today I have Garrett Brown here with me, BiggerPockets short-term rental expert and host of the brand new bigger stays YouTube channel. Garrett, how are you?

Garrett:
I’m doing great. I am super excited to be back talking deals with you, Ashley, and it’s one of my favorite things to do anytime

Ashley:
We have a really fun show lined up for you guys today. I gave Garrett some homework and he brought three real on-market deals with him. They’re in three different locations and at three different price points, we’ll analyze each one as both a short-term rental and as a long-term rental. So you can see the pros and cons of each strategy. Along the way, we’ll share a few key methods we use to break down deals that you might be missing in your own property analysis. Okay, Garrett, are you ready?

Garrett:
Born ready.

Ashley:
Okay, so Garrett, what is the first deal that you brought us today to analyze?

Garrett:
So the first deal is in Fredericksburg, Texas, which this city rings bells with anybody within Texas of a travel destination here, but maybe not for other people. This is one of the highest performing short-term rental markets in the country, but it’s also about 30 minutes away from Austin, Texas, and it’s its own booming metropolis in many ways. It has many wineries. It’s like a really cool tourist destination for a lot of people, but it’s grown in just general size in the last few years. So there’s a three bedroom, two bath property that has been on the market for a good bit that I’ve had my eye on. It’s about 1800 square feet and it’s priced at about 449,000 right now, but when I analyze it as a short-term rental, it can project the revenue of being almost $74,000, which the shocking part about that is that’s actually one of the lower projected revenues in the neighborhood that it’s in.

Garrett:
There’s a few of ’em that are performing with $120,000 a year revenue, a hundred thousand dollars a year revenue, but the secret sauce for short-term rentals is it’s the purchase price. I don’t want to say it’s irrelevant with short-term rentals, but the thing that really pushes the needle and how you can get up to that a hundred thousand, 120,000 gross revenue mind you per year is the amenities that you add and then being able to get your average daily rate and your occupancy goals up. Air DNA, they’re kind of the short-term rental data expert for a lack of better words within the industry, and their projections are it’s going to have a 46% occupancy rate with a $437 average daily rate, which is what you could bring in as a short-term rental. But the key with Air DNA, and they’ll tell you this themselves, is that’s just a baseline number.

Garrett:
You want to go in and really analyze your competition and comparables that are nearby. And after I did that using Air DNA and tools like Airbnb, I see that something as simple as adding a hot tub and making the backyard just a little nicer and welcoming. That’s how you could probably get to that a hundred thousand, 120,000 revenue side that we’re kind of looking for because my current cash on cash projection, if we just use the baseline air DNA numbers is pretty low. It’s close to about 1%, which is, I would never say anybody to do that deal, but where the true short-term rental investors and the ones that have been winning in some markets is they go in and to analyze these and actually you’re able to beat the air DNA projections quite a bit if you’re able to analyze your competition and see what they are doing so well that is getting them to that top of the market to reach that a hundred thousand, 120,000 that we’re hoping for. If we add a few simple amenities and keep our renovation cost and furnishings in line, we should be able to get it up to closer to about 15%.

Ashley:
Well, first I want to point out how you’re taking into account the operational piece. So you’re looking at the numbers of this property and on the rookie podcast we constantly stress what do the numbers say? Stick to the numbers, don’t get emotional about a property, but I think the difference between a long-term rental and short-term rental is that you have that hospitality piece, that operational piece where you are able to almost manipulate the numbers in a different sense because of that operational piece where as long-term rentals, yes, you can have a better performing property because it has nicer amenities or your better property manager people will pay more to stay there, whatever that may be, it’s not going to move the needle that much. You have to stick to your projected rents where in your case you can manipulate to actually make the deal work for you based on the operations. And I think that’s a really, really unique strategy. And what is your advice on if you’re a rookie investor going to buy your short-term rental? Should you bank on that or should you wait until you get some experience under your belt before you’re tying in that operational piece into your deal analysis?

Garrett:
I always tell people that are potential investors and things to analyze it from a short-term rental side with the operations from day one, but then also make sure if you’re newer to this and you’re not a hundred percent certain on a market or different things, or even if short-term rentals are the strategy you want to go after, you want to make sure that it can also possibly work as a long-term rental or even a midterm rental because you want a few different exit strategies, especially when you’re newer to this type of investing. There’s a lot to it that you may not expect. And so if this is a strategy that’s brand new to you, I think when you’re looking at some of these type of deals, analyzing it from the midterm rental and the long-term rental side is going to be extremely invaluable so that you can pivot if it’s ever needed.

Ashley:
That’s a great point to have those exit strategies in place. And one thing I think that I want to make clear too is that when I say Garrett takes into that operational piece and how he can make the property unique, he’s still looking at the numbers. He’s just looking at the higher end because he’s going to be able to get more. It’s not that he’s completely winging it and saying, oh, my unique skill is worth $200 more a night. It’s still looking at the numbers, but instead of taking what that median rent is or the average rent of the property, he’s going towards a higher end of the better performing properties. He knows he can get it

Garrett:
There. Like I said, there’s his projected about 74,000. I’m very confident that I can beat that number because there’s proven comps within a few block radius four or five that are doing 90,000, a hundred thousand, 110,000. So that’s how I have the confidence that I can get to there. But if you didn’t see the comparables that are showing that your chances of just adding a few amenities and hitting that number start to dwindle down. So you just need to look at it from all perspectives and make sure there are comps that can support what you’re planning on trying to do.

Ashley:
Well, I wish I was as confident as Garrett that I could make this work as a long-term rental, but looking over this deal, so the first thing I did, I went to the biggerpockets.com/rent estimator and I put in the property address, I put in the bed bath count, and it’s telling me the median rent is $2,490 per month on the low level 1200 to the high level, 3,200. So that’s kind of a wide margin, but the majority, it kind of shows you the graph of where each of these places are. Very, very small amount are in that high 3,200. Maybe if you went in and did an extensive rehab on this property, you could get that to the high end, but then we’re just adding more and more money that we need to put into this deal and refinance autumn. So then I went and I did, what would I estimate the mortgage payment to be?

Ashley:
So I just did general 20% down 30 year fix at a 6.63% rate, which honestly if you’re going to use this for an investment property, it’s probably going to be higher, but that came out to be $2,200 a month just for the principal and interest, and then taxes ended up being 3 78 per month. Home insurance about one 50, and that’s just kind of going off an estimate. So this deal does not pencil out because already your monthly payments not including anything else besides taxes, insurance principle and interest is going to be about 2,800. On the lower end, you might have a higher interest rate that increases that or higher insurance because insurance rates are increasing. So I’m going to do thumbs down. No, this would not work as a long-term rental.

Garrett:
I can agree with that. This is definitely a very, if you’re a short-term rental investor that has a little experience, this is a great market for you. Otherwise, I think there’s a better option coming in deal three that I think might be a little more appetizing for long-term renters.

Ashley:
Okay. Well, we’re heading across the country from Texas to the Pacific Northwest for Garrett’s next deal, but first we must take a quick break. We’ll be right back.

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Ashley:
Okay, Garrett, tell us about deal number two. We’re in the Pacific Northwest right now. What area is this in?

Garrett:
So this is in Wheeler, Oregon Market. I have never invested into the Pacific Northwest, but I’ve always just been completely enamored with the beauty of nature they have out there, the amount of national parks, state parks, and the vast amount of tourism they have that is driving out there. So this is a new market and area that I’ve been exploring some. They have a tremendous amount of tourism that comes in there. It’s a three, two, it’s about 1300 square feet, but one of the coolest thing, and when you’re thinking from a short-term rental perspective, which my brain always goes there, especially now that I have been doing this for so long in the short-term rental side, this has a really immaculate ocean view and mountain view. If there’s a view, your chances of becoming a successful short-term rental, when I say a view like a spectacular view, this shoot through the roof.

Garrett:
And so this has that wow factor to me and it’s in a great area that has very high occupancy and can achieve very high average daily rates. And there’s even an opportunity that you might be able to maybe place a tiny home unit or an A DU unit on side of it looking into the permitting and what the deed restrictions are in that area. It’s going for about 339,000 spent on the market for a little bit. So you never know there might be some wiggle room there. It’s projected to have revenue of about $65,000 annually per year. The occupancy rates are pretty good. They’re about 55% according to Air DNA. The average daily rate’s pretty good. It’s about $330 according to air DNA as well. The cash on cash projection for this property is not significantly high. Just using the baseline numbers from Air DNA, it’s about 4%, and I’m not as confident as I am with the Fredericksburg market by looking at some of the comparables that I can add some amenities, do some extra things to get it to maybe a hundred thousand a year like I was in the Fredericksburg market because the nearby comparables are making about the same that air DNA already projected.

Garrett:
It’s one of those things where you could add a hot tub, I’m sure, and probably get your amenities and occupancy up. My goal would be to get it to 12% cash on cash return, but I’m not as confident in this market based on what I’m seeing with the comparables nearby. So if we’re able to negotiate the property price down and maybe get some seller credits, then I might be able to help the cash on cash return, but those don’t move the needle too much in short term rentals. Getting your occupancy up and your average daily rate is really how you maximize your cash on cash return specifically for short-term rentals. And I’m not as confident in this area now, so I’ve been looking at this deal just because the view and being able to probably be the highest performing in the market, but I’m a little worried that I’ll still never be able to hit the exact revenue goals that I’m hoping for. What it takes with the operation side too of hospitality and short-term rentals, what are you kind of seeing from what you’re looking into on the long-term side and everything else?

Ashley:
Yeah, so the first thing about the negotiation piece, if you have a great agent, it’s already been on the market for 58 days, so maybe there is a little wiggle room there, but I did the same thing I did the last one, I put it into the rent estimator said $1,100 per month on the low end, 7 96 and then kind of on the high end was 1300, and then it was very weird, but there was two properties that were actually getting over 3000 a month. So

Ashley:
Those, I don’t know if they were elicit as fully furnished or what, but that I think kind of skewed the data a little bit. So we’re going to take $1,100 per month for this property, then we’re going to go look at what the mortgage payment would be on this property. So I did kind of the same rules I did last time. The mortgage payment ended up being about $2,000 per month with property taxes and insurance included. So already this doesn’t pencil out your looking at about and $900 deficit in cashflow every single month, but there was something that piqued my interest and could make this deal work. So in the listing it mentions that you could potentially divide the lot, it’s a hundred by a hundred lot and you could build an additional structure. But what I think that you could do with this, you go to the planning board, you’d ask for that, the parcel to be divided, parceled off into its own separate piece, and I sell that lot, especially as a long-term rental.

Ashley:
I don’t need a big lot. You can maybe get a little bit more in rent. I mean, this definitely is market dependent and I’d have to look into more of what people expect when they’re renting, but the bigger the lot, the more you have to maintain as the landlord. Even if you tell the residents their job to maintain it, it doesn’t mean they’re always going to trim the bushes, cut the grass, do all these things to take care of a bigger lot. So I see the opportunity to parcel this lot and list it for sale, sell that, let somebody else build their own structure on that, but use the cash from that to offset some of the costs of this property, and that could bring your monthly payment down and that could actually make the deal work too.

Garrett:
You also could combine strategies too. I have a property that one of my most successful ones is a piece of land that I divided some and I have a long-term rental on it and a short-term rental and the long-term rental tenant, which you have to find the right person, and there’s a myriad of things that come up. They actually help me run some of my short-term rentals and they also rent from me for the long-term rental, and I give ’em a little bit of a discounted rate and we work out some payment things on a 10 99, but you also can mix strategies as well and possibly find something that can work for a little bit of both, especially if you’re able to split the lot and get added value on both sides. There’s a myriad of ways within real estate that you can be creative and make a deal work to the’s highest and fullest potential and balance out the risk and rewards.

Ashley:
Well, we have one more deal to share today, which is at an even lower price point. It’s well under 300,000, but first we’re going to take our last break. We’ll be right back in a few minutes. Okay. Welcome back from our short break, and we are here with Garrett who has brought us a couple deals today and we’re going to be talking about the third one now. So where is the third deal today, Garrett?

Garrett:
This is in Waco, Texas, which I’m not sure if we have any Chip and Joanna Gaines fans.

Ashley:
I was just going to ask, is that from

Garrett:
Fixer Upgrade? Yes, that is absolutely. So it kind of blows my mind and I’m a native Texan for a long time, how popular Waco has become in the last maybe 10 years, and a lot of it is solely dedicated to Chip and Joanna Gaines. They have built an amazing infrastructure out there. That’s where all the fixer upper episodes were filmed for most of ’em. So it’s become a pretty popular destination because they’ve added a lot of other things too. They have some really cool tourist destination, like these old silos that people go tour. There’s a lot. It’s kind of hustling, bustling. It’s near all the major metro hubs of Dallas, Austin and Houston. It’s kind of like a midway point for all of them. So it’s become a pretty popular short-term rental market, but it also has a lot of real estate metrics overall that make a great area in general from long-term to midterm rentals.

Garrett:
And I’ve had my eye in this area for a while. This property is a three two, it’s about 1400 square feet. One thing I really like about this property is that it comes furnished. You’re spend a lot of money upfront when you’re furnishing a short-term rental, and I did a breakdown on bigger stays YouTube channel, talking about how much it actually costs to start a short-term rental business, one that you own, and one of the biggest price differences that comes in is when you have to furnish it yourself. If you get into a property that already has furniture, the cash you’re having to put out immediately is almost cut in half sometimes depending on how the price point something like this, it’s going to be close to that. So it’s listed at about 2 75. This is not a vacation destination only area like the other two that we kind of mentioned first.

Garrett:
Those were definitely more tourist vacation areas, predominantly this one has metrics all around. The occupancy is pretty good. It’s about 52% according to Air DNA. The average daily rate is around $220. So they’re a little bit on the lower end, but there’s not much renovation that you need to put into it and there’s not much furniture that you need to put into it. Maybe $10,000 each for both of them. The issue here that I want people to pay attention to for when you’re getting into this type of market that may not fully be a vacation destination area is Waco has started to crack down on the amount of short-term rentals that are able to get permits in the area. I was able to look at the city code, look at their short-term rental restrictions and different compliances they put together. They’re usually available online. A simple Google search can at least find most of it, just type in Waco short-term rental regulations.

Garrett:
This property sits on a street that you’re able to do short-term rentals on. So I’m looking at the competition nearby. There’s a few of them that have gotten to 52,000. There’s two of them that one does 60,000, another one does 65,000 gross revenue annually. So I at least know there’s a little upside compared to what Air DNA is projecting at the 42,000. When I’m looking at a short-term rental, I really want to see if the backyard has room for improvement. There’s usually two reasons why people will book short-term rentals over a hotel, especially in this type of area. If you have a really cool backyard that has the amenities that cannot be provided privately at a hotel, and if you have a stellar kitchen, that’s the one thing I always tell people is your kitchen, you need to have all the utensils and it needs to be nice because this is one selling point versus somebody going book a hotel with their family is that you have the kitchen and backyard.

Garrett:
If you look at the cash on cash return for this type of project though, it is definitely nothing that I would personally want to get into for this exact property from a short-term rental side because even with the furniture in it and not having to spend much on it, you’re going to be looking at probably a negative 15% cash on cash return, which immediately turns you off. And my brain was like, okay, maybe I can get to that 60 to $65,000 annually that a few properties are doing nearby as well. But even if I got close to what they were doing, I’m still probably at around a four or 5% cash on cash return. So I started to pivot and think like, okay, if I was going to really go into this deal, I do love the Waco market and I think this is a great property for numerous different reasons.

Garrett:
This would be one that I might possibly look into the midterm rental side because there’s a lot of hospitals over there between all of the Chip and Janna Gaines dynamics that they’re bringing in over there. There’s actually a pretty high influx of midterm renters going into this market looking for furnished properties. And I think that I could probably cashflow as a midterm rental, which is a lot less on the operation side than it is a short-term rental. Something in the, maybe this is just cashflow after mortgage and other things are taken out. We probably could get in between three to 4,000 per month. And so I’m sure you probably have been analyzing to see what it looks like as a long-term rental. So I’d be curious what your thoughts are between some of the different short-term midterm rental ideas I had, or if you think this is maybe a better long-term rental play.

Ashley:
Yeah, actually, after you mentioned the midterm rental, I went to Furnish Finder

Ashley:
And I looked in here what it would be, and it looks like just for a two bedroom, it’s going for around 2200 per a month. So I think you could get a very decent rate with a three bedroom here for a midterm rental on the long-term rental side. I went again to the rent estimator. It says about 1600 per a month, but it’s pretty confident in its score. It’s showing that there’s quite a few properties that are in that kind of realm. There’s one that’s priced super high at 2300, and then the lowest is about 1100. When you go to the monthly payment on this property, you’re looking about $2,100. So just comparing those two numbers, they don’t work. But I did see in the listing that it is located near a university, so maybe there is that option for midterm rental if you have adjunct professors coming in or something like that. But I did think too that I believe that 2025, the hottest strategy is short-term rentals were, for a while, glamping was midterm rentals were, and I think this is the year that co-living, so this is a pretty nice property. One thing that I would’ve liked to see is this kind of has an open floor plan where there’s a huge opportunity to take a single family home and turn if it has a separate dining room, turn the dining room into another bedroom.

Garrett:
I didn’t even mention that Waco is home of Baylor University, which is a major university within Texas, so the midterm rental market and co-living. I think those could be great options to explore in this, and it’s been on the market for a good bit too as well. So this is another one, working with a highly qualified agent through the BiggerPockets agent finder, you will probably have a lot of leverage to work on that negotiation, the purchase price or do seller credits. And so there’s a lot of options When something has been stale for a little bit and coming furnished is actually might work in your favor, that might not be as appealing to other people looking to properly buy this property.

Ashley:
Yeah, 245 days spent on market. Doesn’t that automatically make you think what’s wrong with it?

Garrett:
And

Ashley:
It

Garrett:
Could

Ashley:
Be nothing. It could be nothing wrong with it.

Garrett:
You’ll be shocked sometimes. Luckily, I’m an agent and so I can always make offers on properties I like and not feel bad of making my agent like, oh, make low ball efforts, but you’ll be shocked at some of the offers I’ll put out there sometimes and they’ll entertain it. Maybe they’re finally getting to that point now where they’re like, all right, I’m at my wits end. Let’s see if somebody has a deal for me. So there’s nothing wrong with working with a good agent, setting that standard with them and telling them, I’m going to buy something. I might low ball a few. Don’t hate me for that. And most agents, if they’re an investor friendly agent that the ones that come from BiggerPockets Agent Finder, they’re going to fully understand that strategy and also help you really understand that market list prices are just a suggestion. So you give your suggestion for what you think it’s worth and stick to your numbers. If you have a number, once you do your deal analysis that you’re like, I like this property, but I would only buy it at 2 35, don’t get emotional, don’t go above

Ashley:
That

Garrett:
And go to the next one. Get your repetitions in, and this will start to slowly work your investing memory muscle, and then you’ll eventually be able to knock a few of those deals out the park and a few of ’em will start going your way. It’s a numbers game. Sometimes

Ashley:
You’ll be way more emotional with a property when it performs really well and cash is great than if you just liked it when you walked through for the showing. Yeah,

Garrett:
Absolutely. You’ll be way more emotional if you buy the wrong deal, so that’s why you stick to your numbers.

Ashley:
Well, Garrett, thank you so much for bringing those deals on today and for sharing with us. Thanks to everyone for listening to the show today. I’ll see you over on the Real Estate Rookie Channel, and you can find Garrett on his new channel, bigger Stays on YouTube. Dave Meyer will be back soon with another episode of the BiggerPockets Real Estate Podcast in a few days. Thanks for watching.