Ep. 77 | Short-Term Rental (STR) Loophole Explained

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Welcome to the Teaching Tax Flow podcast, where the goal is to empower and educate you to legally and ethically minimize taxes paid over your lifetime. Hey everybody.

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And welcome back to the podcast today, episode 77. We are going to look at those STR loopholes, but little bit of information for you. You are only a couple weeks away from that tax deadline or some refer to as tax day.

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However, go back to episode 25 we did here and on a year ago, almost to the date, check it out, the value of a tax extension. But before we jump into today’s topic, let’s take a brief moment as always, and thank our episode sponsor.

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This podcast is sponsored by The Mortgage Shop. Are you looking to qualify for an investment credit loan without jumping through hoops? That’s easy. They have loans with LTV up to 89.99%. Exploring their products and discovering how they can work for you is simple.

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Hey, everybody, and welcome back to the Teaching Tax Flow podcast. As you’ve seen in the title, the show notes, etcetera, and in the intro that you just heard, today, we are gonna talk about the STR loophole. So acronyms you know we love in the teaching tax for world. I mean, heck, the IRS has 1, internal revenue service. They go by IRS.

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Naturally, we love our acronyms. STR, short term rental. So STR loopholes, today, we are gonna explain those and what they are, what they aren’t, and we got a great guest. But before we introduce him, Chris Pacuro, you know what I’m gonna say. Welcome back to your own show.

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How’s it going?

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Thank you for welcoming back to the to our show, Johnny t. I appreciate it. Very excited about our guest today, and we have had a ton of people in the Teaching Tax Law community. And actually, I I believe our our any of our content on short term rental tax, strategy or loophole is is in our top three of consumption. So we knew we have we we’ve been wanting to do this topic for 6 months where we wanted to wait till we had a guest that not only lives and breathes in this space, but also can give our listeners some practical tips at the towards the end of the podcast on what to do next.

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And and, this is a strategy that we’ve used personally, and it’s really exciting. And and, ultimately, it allows taxpayers that invest in qualified short term rental properties to utilize cost segregation studies to and potentially offset w two wages or retirement income or any any type of other income and navigate around the passive activity rules. But Arta’s gonna explain that to you, as well. And and, yeah, we’re very excited to have, Arda Birkin, join us. Arda, welcome to the show, and can

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you give us a little bit of history about yourself and how you found yourself operating and and running and cohosting short term rental properties.

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Thanks for the kind introduction and great to be with you guys today. I’m a real estate investor. I also build a short term rental business from scratch inside Florida. Back in 2020, I own a real estate consulting firm named Short Term Rental loophole.

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The main reason I got into short term rental business and launched my own consulting practice is because short term rental properties are a great investment for high income earners. They deliver, strong cash on cash returns and underlying assets often, appreciate. To give you an idea, my first short term rental in South Florida, generated 210 k revenue and the net income was about $63,000 in the 1st year of operation. You know, obviously those, you know, that kind of numbers were impressive. That excite me the cash flow, you know, like, than I wanted to, you know, like kind of get from, you know, like, the first property.

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So but in addition to that, short term rentals are also offered, you know, like those with high w two income and massive opportunity to reduce their tax burden.

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And I’m gonna touch on what it what makes a property a short term rentals according to the IRS, because typically rental properties, like I said, are are passive investments, and they are considered so you you have the passive activity loss rules that you tangle with, meaning if you have losses for rental properties. Now we know in teaching tax flow the one of the one of the laws of the cash flow doesn’t equal tax flow. So you could very well have a rental property that is a positive cash flow, putting money in your pocket, but on your tax return shows a loss. And that loss is due to the depreciation deduction, And that depreciation deduction can be fueled by using bonus depreciation, which is further fueled by using a cost segregation study. So let’s say you have a rental property that’s putting cash in your pocket, but you put a lot of money in there to start up.

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You got some furniture, fixtures, you bought it maybe even bought a turnkey, and you have a large depreciation deduction. Well, in order to avoid, I should say, and legally and ethically avoid the the passive activity rules, if the property is considered a short term rental property, then it’s considered a commercial operation, if you will. So what makes a short term rental property? Well, there’s a few different components. The first component’s gonna be the average length of stay of the tenant.

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So the if the average length of stay is of the tenant is 7 days or less, you’re typically going to have a short term rental property. Or if the average day is 30 days or less and you are providing substantial services. That’s a very, very rare think about that situation would be as if you owned a property, or let’s say you owned a big lot and and you have 4 cabins on it and you live in the 5th cabin and you’re the one changing the seat sheets, preparing the meals, extremely, extremely hands on with the guests. So typically it’s gonna be that 7 days or less. There are some rules as far as how many days you could stay in there.

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Personally, it’s gotta be 14 days or less or or less than 10% of the use days. But typically, you’re talking about a vacation rental, and you also have to have something called the material participation. And this is this is very important. So to obtain material participation, and we have some resources as far as how to track these hours, there are 7 different tests. The the easiest test and the most likely test you’re gonna pass when you’re dealing with a short term rental property is the 100 hour rule.

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What the 100 hour rule says is that you’ve put in at least a 100 hours of time into operating that short term rental property, and you have more time than anyone else on that property. And you’re putting the post on Airbnb, VRBO, or use software like hospitable or or or any of these softwares that manage your your reservations and your client communications, then you’re most likely meeting that material participation threshold. So if you meet that material participation, you have a short term rental property, thus the loophole, and then you could potentially, you could potentially show a large loss from that rental property with the cost segregation. So I need to offset, as Artis said, high w two wages. So let’s say you have a 1 a a couple and the one spouse says a $900,000 of w two wages, the other one is a homemaker but runs the Airbnb property, even and it could be remotely run, you could potentially have 100 of 1,000 of dollars of losses from that short term rental property and offset the w two wages.

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So, hopefully, I explained it in a in a fashion that’s kinda digestible.

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And, Chris, really quick too before before we go too far on. So me being, you know, not the tax guy, the voice of the average Joe. Right? So just to clarify. Right?

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We’re talking about some of the the short term rental loophole. So to some people and I know we mentioned this, maybe, like, a dozen or so episodes back and clarified there too. When we talk about loophole, we’re not saying like, oh, this is a, hey. I gotcha, uncle Sam, and doing anything unethical. This is basically just navigating our way through the text, quote, unquote, system.

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Is that correct, or am I totally off on that?

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You know, like an excellent explanation, I believe, but, very basically, the short term rental loophole, which refers to a section of the tax code that says if the average customer stay at a short term rental for 7 day or less, then your short term rental is not a rental activity for the purpose of the tax code. It’s treated as any other business. Ultimately, that means, like Chris explained very well, all you need to do is materially participate in that business for the losses to be non passive and offset your w two income.

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Absolutely. So now we’ve defined that. Arda, I wanna I wanna pick your brain because this is your wheelhouse. For someone listening to this, what are the things and and feel free to to mention certain markets, but what are the things people should look for when selecting? I’m gonna first start with a market and then start with a property because you are very good at analyzing that that what we call COC, cash on cash CNC, cash on cash return.

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You know, there’s there’s properties by the beach and theme parks and mountain, and there’s condos and 2 bedrooms and 3 bedrooms. So first, you know, what what type of, in there somewhere that we’re seasonal. So what type of market are we looking for, typically, in in you might say, well, it depends on the price point. Right? And then what type of property

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are are you seeing that are getting the best returns? It’s a great question. And, you know, like, again, investing in short term rentals can be an incredibly effective way to save money on your taxes. And buying a short term rental and expanding your earning potential by accumulating additional properties, a gate plan used by a fine network individuals nationwide. Right?

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But when we talk about, you know, like the, cash on cash returns, ROIs, you know, like the number that I really focus on, at least I would like to see a 15, you know, like or 20% cash on cash return and I strongly recommend, like purchasing a single family home, a larger property, preferably, you know, like at least 4, preferably, you know, like in a 5 bedroom due to the fact that you can generate more revenue, from that particular, you know, like in a property compared to a 2 or 3 bedroom. Because when I look at the, you know, like the short term rental markets, usually every single market nowadays is saturated, right? But when you talk about, you know, like on a larger properties, 5 bedroom, you know, like or 6 bedroom, the competition is much less. So it would give you the, you know, like, the opportunity to charge, you know, like, more, average data rates, which would, increase your gross revenue if you look at it from an, you know, like an annual prospect. It’s a

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great point, and I and I’ve heard that quite a bit where you’re buying buying a studio, buying a 1 bedroom, buying a 2 bedroom unit, you know, is a good entry point potentially cost wise. But you’re also then competing against hotel rooms. You’re competing against even a a a room at a, you know, Residence Inn that’s a 2 bedroom. So 4 or 5 bedrooms are gonna be better for a bigger party. So what market so I I do like that, and I guess it depends.

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You know, there’s certain markets that don’t have a lot of big chain hotels. So what markets are you seeing? What should someone look for in a market? Should someone, that’s gonna self manage your property be concerned about being able to drive to the property, or or is is distance an an issue, or or is it some more picking the right market?

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It it really boils down to, you know, like, determining the budget. You’ll need to know how much money, you know, you can work with and what price range you’ll be looking in, and that will impact the type of property you can search for and the area you will be looking in. You know, I always tell, you know, like an investor establishing a budget upfront will save many headaches in the long run and get you aligned with your goals. But to answer your question, I do like, you know, like, in a certain markets. One of them is North Carolina, especially Asheville area because, like, I’ve been seeing, you know, like, really good, you know, like, kind of cash on cash returns, ROIs, you know, like, in that particular market.

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Have you been, you know, like, kind of chasing deals typically, you know, like in the Asheville area? But obviously, location, location, location. Again, you know, like kind of when I look at, you know, like the Asheville market, you know, like the proximity or the vistas between the downtown Asheville and your property, you know, that would be the determining factors because it’s gonna affect your, the rates, you know, like, you can charge on a daily basis besides, you know, like, on a North Carolina and Asheville, you know, Montana, it’s and Maine, you know, those markets are not very saturated and, you know, like you were able to find actually very nice, you know, like properties, large, you know, kind of single family homes, you know, like in those markets.

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So you’ve got different markets. Right? So some markets, like, I’m going to give you, like, the middle the Orlando market seems to be the occupancy rates are super high, but, you know, revenue per per night’s low. So, obviously, something to consider and we considered as well is that, you know, don’t be so focused on occupancy percentage because that just means there’s a lot more foot traffic. Right?

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Focus on your your revenue and your average nightly, you know, revenue, which the next question is gonna kinda tie into that is, what amenities are you seeing are most in demand in in this in are most properties that perform well? Is is theming, in your opinion, the property of value to a potential buyer? Great question. So, you

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know, like, obviously if you are talking about Orlando, I would say, you definitely need a pool. In addition to that, I would say you would need, you know, like a pool heater because during the, you know, like the winter months, that’s what we call, you know, the high season in Florida. If you are catering to, you know, like on the high end customers, the, you know, like the temperatures drop during, you know, like January, February, March. You need to be able to, you know, like offer that, you know, like on a nice amenity, a private pool as well as a, you know, like a pool heater. But in addition to that, I’ve been seeing, especially Asheville, North Carolina market, you know, a TV room.

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And when I say a TV room, a luxury, you know, like on a TV room with big chairs, big you know, like, on a screen, nice, you know, like, outdoor patio with a firepads because it creates, you know, like, the that amazing, you know, like, an ambiance. Due to the, you know, like, the global warming, I was saying, it doesn’t get that cold right now, you know, like, we are in March. Right? I’m in Nashville, but I was in North Carolina about 2 weeks ago, and it was a lovely day. And after 5, 6 PM, if you have them, you know, like the heaters, you know, like an outdoor heaters, then you can definitely, you know, like, hang out hang out outside and, you know, like, you can watch, you know, like, the beautiful views.

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But so so those are, you know, like, the amenities, you know, like, that come to my mind. But, if you are looking at a property in, you know, Maine or Montana, definitely a hot tub, you know, that kinda would be a great, you know, like amenity.

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No. I agree that that it really just depends on I mean, some type of pool or hot tub is is going to be nice because if someone’s renting a a home, they want their privacy to have their own pool, instead of using a a hotel pool, if you will. So, and that’s, you know, that’s really important. Let’s talk about the owner side. In your opinion, what are some of the relationships locally that are important to establish?

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Obviously, people are concerned about cleaners and handymen and in their, you know, the operation. Let’s say you’re managing the property remotely. What are some of those key relationship that you would need

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to build as an, you know, like a short term rental investor, you know, like a relationship that you would need to build as an, you know, like a short term rental investor is finding, you know, like the top notch cleaners. Because, just imagine, if it’s like, you know, like a luxury property, you checked into the property and if it’s not, you know, like extremely clean or if it doesn’t feel clean then it’s gonna create, you know, like a tremendous amount of discomfort for, you know, like your guests. That’s not something that you wanna run into. So, I strongly, you know, like I’m going to comment, I’m not a big fan of actually leveraging, you know, like, cleaning companies. What we did inside Fyodor that we really focused on, you know, like the local neighborhood cleaners and, you know, like we negotiated, you know, like kind of different deals with them.

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Obviously, whatever, you know, like they, delivered, you know, like the services that we were looking for, we tipped down well and we leveraged their services more. But from my point of view, definitely you need to have multiple different, you know, like kind of cleaning crews due to the fact that anything could happen. You know, like, they may get sick. They may, you know, like, kinda need to rot. You know, like, they they are, you know, like, their situation kind of different.

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Right? They would they they may, you know, like, kind of over commit or whatever the reason is. So you need to have a backup plan. Right? That’s the one thing.

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The second, you know, like, kind of most important relationship that you need to have as a, you know, like a short term rental investor in the local market that you’re operating is the handyman And what I would, what I did, you know, like in Sadfrid, I literally knock on, you know, like my neighbor’s doors and ask them, you know, like handyman your commendations Because, like, you could use Google, you could use Yelp, but nowadays, you know, like, everybody talks straight about, you know, like, on everybody’s service. Then, you know, like the neighbor tells me he’s been, you know, like kind of leveraging a certain handyman and, you know, like he’s on time, he does a good job, he’s reliable, that’s, you know, like the handyman that I want to work with. So that’s how, you know, like I was able to build, you know, like kind of strong relationships and, you know, like that’s how I built, you know, that kind of team and obviously we replicate, you know, like the same thing in other markets and that’s how, you know, like kind of we delivering like a certain customer experience. That’s what it really boils down to on Airbnb or VRBO.

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That’s how you need to differentiate yourself from them, other, you know, like kind of operators.

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Yeah. I mean, having the handyman and having the, cleaners is huge. And, you know, some of that even though I’m in this world somewhat on my own, having a redundancy is really important. Just think like you said. I mean, we’re all human, so we are unreliable even if we wanna be reliable.

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We’re just unreliable. Like, anything could happen.

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Yeah. Exactly. And over the weekends, you know, like, I mean, you would need some help. Right, like, it could be Sunday, it could be, you know, like, on a Saturday, and the same thing, you know, like, something could break down. You need to have that, you know, like, kind of support system, you know, like, in place.

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And the best way to, you know, like, kind of develop those relationships is basically leveraging other people’s relationships in the neighborhood. And as long as you’re not you’re a good neighbor, you know, like, you’re not gonna have any problems getting those, you know, like, under referrals from the other folks based on my experience.

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And, Art, I actually have a question for you too. So we you talked a little bit about or actually, Chris, I think you had mentioned it too. Right? Like, obviously, it takes it takes cash to invest. Well, not necessarily, but you obviously need resources to invest.

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In your experience, kind of aligning or or finding those investors in a sense who are willing and knowledgeable enough to invest in short term rentals. Have a lot of the people and and individuals that you’ve talked to, families, etcetera, are they even aware that short term rentals really are a great investment on their side? And then to follow that up too. So, So obviously, are are a lot of them aware of it. But then also, in conversations with them, what are some of the concerns they might have?

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Is it a, oh, I completely wanna be hands off. This sounds like it’s too much work for me. So maybe walk us through that a little bit for our listeners that, you know, maybe you’ve been looking for something like this, but never truly looked at it as an opportunity that they could take advantage of.

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Based on my experience, most of the investors, do not have the expertise to analyze markets and deals properly. And I’m not trying to be harsh but, you know, like, I have to not kind of point that out. They also don’t know how to buy a short term rental property the right way. And also what I’ve been seeing, most of them lack an understanding of the tax code. I mean, from my point of view, finding the highest profitable short term rental property and then buying it right way, using it for non passive losses and leveraging, you know, like advanced hack strategies are not straightforward issues.

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And these are often, you know, like, these are often huge amounts of money at stake. So it makes people, you know, kind of very nervous, right, including myself. So what I can tell, it really requires the help of a team. I would say it’s specifically a real estate CPA and a short term rental, you know, like, investment ex

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it’s funny, you know, here here I am in the middle. So we got a great CPA and a STR expert right

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here on the show. So no. This is this is great. Yeah. It’s interesting because I mean, I’m just I’ve loved real estate since I was 5 years old playing monopoly.

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And so wherever I go, I’m always interested in the market. Even if I’m not really gonna purchase a property there, I just it fascinates me and then I’m always straight thinking like, okay. Well, you know, and I think a lot of times what happens with people that aren’t, you know, working with a professional, and realize that there are people like Arda out there, that that I that can help them analyze the property. Because a lot of times what I see from the from from my perspective is I like going to the Smoky Mountains. I like going to Orlando or the beach, you know, in a family.

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Well, we’re we’re going twice a year. We’re paying all this money to stay there, and and then they start looking around. I mean, we should buy something, and they the they’re kinda influenced by their heart more than their head a little bit when they’re buying the property. So, before John wraps us up here, Artie, can you kinda talk about, you know, what are some of the things that you do as and we’re gonna leave that information, you know, in our show notes. But what are the thing some of the things you do?

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Because you work specifically with investors on market selection and property selection. So what are some of the things that you help them understand and maybe go on that go beyond the emotional part of of the property and location. This is the,

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you know, like the $1,000,000 question, right? Like, and, you know, very, you know, like kind of briefly, being successful in real estate investing largely comes down to the property that is chosen. And a successful investment property is the one that provides the highest ROI for the longest period of time and proceeds in it well. We basically, me and my team, we handle all aspects of finding the most profitable short term rental investment property. From deep market research, lending you the highest profit, profitable, property, teaching you, furnishing and managing your property.

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So that’s what, you know, like kind of we do and that’s what, we are really good at.

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So, Artur, this is one that’s pretty time or I shouldn’t say time sensitive, but time relevant. You know, obviously, we’ll we’ll use Airbnb for example. So anybody that follows the short term rental market obviously has heard about significant changes, through Airbnb. So, again, Airbnb is just one piece of it. Right?

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So looking at New York and we don’t have to get into the political and and too much of the regulations of it, but in turn, maybe talking about how you help navigate through some of those. So looking at New York City, for example, there was a giant blow to the short term rental market when they basically came in and, you know, theoretically swung a, you know, swung a hammer and and wiped it out. So do you find yourself actually, you know what? I’m gonna answer my own question, but then I’m gonna ask you another one. So I know for a fact that you help them navigate those markets.

00:24:57.185 –> 00:25:08.620
So for example, if you have somebody say I’m say I live in Michigan. I really love going to New York City. I looked at it as a dream of owning a short term rental there. You say, hey, John. You know what?

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It’s probably not a good idea right now, you know, based on etcetera, etcetera. So that’s a huge part of what you do, correct, is really helping guide them through, you know, navigating those because more and more markets are getting regulations. Some help, some hinder, right, on on investing.

00:25:26.010 –> 00:25:32.650
Yeah. Absolutely. And let’s talk about, you know, like, kinda just to give you, you know, like, a specific example. Let’s talk about Asheville really quick. Right?

00:25:32.650 –> 00:26:30.700
Like, you cannot run a short term rental within the city limits of Asheville and, you know, like I run into investors, you know, like they are looking at like an assortment properties in Asheville and when I tell them, if you’re not going to buy this property, you know, like there’s going to be a 30 day minimum on this particular home that you are looking at. Oh, we didn’t know that. So you really need to, you know, like, kind of pick up the phone and call, you know, like this city and ask them and get in touch with the right department, the short term rental department, you know, like, and, you know, like have a conversation with them on the phone and get their email address and send them email like a follow-up emails and, you know, like, you know, like give them the address and get their get approvals because email is like a written approval nowadays like and that’s what we do for instance for our clients because honestly I run into, you know, like, so many, you know, like, investors they, you know, are gonna told me that they talked to the real estate agent and they were told that they can operate legally operate a short term rental in a particular market and turned out that that wasn’t the case.

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So, I mean, what I tell them, obviously, if you leverage our services, that’s something, you know, like kind of we look into, you know, like for every single, you know, like an investor and it’s a, you know, like a huge deal, but if you are doing it, you know, like on your own, you must, you know, like gonna pick up the phone, call, you know, like the city and verify the information and give them, you know, like the physical address and ask them, you know, like basically can it be a, you know, like kind of short term rental? I’m looking to, you know, like rent this property on Airbnb or VRV or less than 7 days. Would that be okay? And I mean, based on my experience, because we’ve been looking at, you know, like, kinda so many different micas talking to, you know, that kinda city officials. I never run into a situation where it took more than 24 hours to get a straight answer from them, you know, like the city.

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That would be, you know, like my suggestion or recommendation for, you know, like the real estate investors.

00:27:21.120 –> 00:27:42.850
And, really, the value of working with somebody like yourself. Right? Like, I’m thinking of of here, even, you know, the the smaller town that I live in here. There’s regulations in place that if you were to call the city office well, not here specifically, but if you call a city office, you may get a response from the city and the thumbs up. However, you might be in a neighborhood, HOAs, POAs, etcetera, that say absolutely not.

00:27:42.850 –> 00:28:04.370
Right? So that’s where, you know, your knowledge not only and I’m I’m speaking for you a little bit, but I’m gonna make the assumption. You know, your knowledge as far as for not just knowing the answer, but knowing how to get the answer and who to talk to and and really how to navigate it is huge. So, on that note, I don’t wanna cut anybody off. However, I know we can talk on this forever.

00:28:04.590 –> 00:28:12.980
So, Chris, do you have anything else you you wanted to ask Artie here before we before we skip along? Because I know we’re gonna have to do another show on this one for sure because I have all kinds of questions.

00:28:12.980 –> 00:28:30.585
Right. Absolutely. I wanna thank them for coming on the show. And, you know, if you’re listening to this, we either own a short term rental property or you’re deeply considering it, please reach out to us and and we can we can help guide you in the right direction, and and you’ll pay a lot less tuition. Tuition is money you pay to learn something that is very expensive.

00:28:31.820 –> 00:28:56.655
And exactly. There’s there are several as you as you heard on this podcast, there are several considerations when when deploying the strategy in this the special sauce of teaching tax quo is that we help people in our community implement a strategy. We tell them about it, and we help them implement it. So thanks thanks, Arta and John, and and I hope everyone, jumps in with questions.

00:28:56.795 –> 00:29:14.665
Even my dog’s excited if you can’t hear him in the background. But, Arda Arda, definitely thank you for joining us here on on this show and really, you know, sharing your knowledge on this. Obviously, STRs, so short term rentals, get a little bit more popular in some areas and and retracting a little bit from the others. So we look forward to to having you back soon.

00:29:14.845 –> 00:29:16.765
Yeah. Great to be with you guys. Thank you again.

00:29:16.765 –> 00:29:38.015
Absolutely. And as I always like to close it up here on the Teaching Tax Flow podcast, same time, technically, but a different week. Same day of the week, different topic back here on the teaching tax flow podcast. Hey, everybody. John here from the Teaching Tax Flow team.

00:29:38.360 –> 00:30:09.765
Thank you for joining us here on this episode as we looked at those STRs and STR loopholes with Chris and Arda. And, of course, we make things as easy as we possibly can here. If you are interested in any more information on the STR loophole or really just wanna pick these guys’ brain, you can actually go directly to STR tax. Guru. We’ve made it that simple for you.

00:30:10.065 –> 00:30:23.545
Strtax.guru g u r u. You can literally fill out the form in there. It goes directly to these guys. They’ll get back to you, and they love discussing this topic amongst many others. So, take advantage of that.

00:30:23.545 –> 00:30:40.695
Take advantage of the private Facebook group, defeating taxes.com. We’ll send you directly there, and, as always, keep sending us the show topic information, guest info, anything that you guys wanna hear on the podcast, that’s what we’re here for. So until next time, we’ll see you very soon.

00:30:43.390 –> 00:31:00.915
The content provided is for educational purposes only. We encourage you to seek personalized investment advice from your financial professional. For all tax and legal advice, please consult your CPA or attorney. Investment advisory services are offered through Cabin Advisors, a registered investment adviser. Securities are offered through Cabin Securities, a registered broker dealer.

00:31:02.290 –> 00:31:12.357
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