Hello Everyone - Newbie here(obivously). I'm trying to break into real estate. Money isn't an issue per se as we just downsized our primary so we have money from that. I get the 4 pillars and honestly the STR tax loophole is very appealing as I still have W2 income. BUT, for the life of me I cannot find any STRs that actually cashflow with a mortgage. For example the place will be $600K and generating say $40K in revenue?? Am I just doing it wrong? Any pointers would be awesome as I'm almost ready to just give up.
Is this not possible and I need to hope for the other 3 pillars to outweigh the lack of cashflow? I've looked in Frisco, CO, Traverse City, MI, Ellicottville, NY.
Hi Ryan, and welcome!
Congrats on starting on the road to freedom with real estate.
Question: What's more important than finding your 'perfect' deal? Answer: patience and timing.
Without being patient, staying consistently on the hunt for a good opportunity, you might be able to stumble onto a winner--but that won't keep you in the game long term.
Always be looking, and when you do find the deal, pounce. That's the timing aspect; having your ducks in line so you are able to pull the trigger when you do spot the opportunity.
I've found that the most important part of real estate (besides your knowledge) is your mental attitude. Don't quit, stay encouraged, and NEVER give up. Every potential deal that doesn't work gives you more street smarts and brings you a step closer to that next big beautiful deal.
Lastly, real estate is a neighborhood business. As a beginner, maybe concentrate on the area that you feel most comfortable with. Become an expert in that one area you choose, and speak to as many investors, agents, contractors, sellers, and even buyers as you can. You'll be amazed how leads will come from totally unexpected places.
Hope this helps you a bit. Looking forward to hearing about your first deal! Best of luck!
Hey @Ryan Berg, feel free to reach out if you'd like to chat. Most likely you'll need to identify a STR that you can ad value to. Look for deals that have an ADU, or the possibility of adding an ADU. Can tear down walls to add more bedrooms, can you offer a unique perk/benefit that no other STRs in that area offer? Depends on your strategy, but many investors are also targeting STRs that are smaller (2/2, 2/1, 1/1) so they can pivot to the MTR strategy if needed.
Hi Ryan, and welcome!
Congrats on starting on the road to freedom with real estate.
Question: What's more important than finding your 'perfect' deal? Answer: patience and timing.
Without being patient, staying consistently on the hunt for a good opportunity, you might be able to stumble onto a winner--but that won't keep you in the game long term.
Always be looking, and when you do find the deal, pounce. That's the timing aspect; having your ducks in line so you are able to pull the trigger when you do spot the opportunity.
I've found that the most important part of real estate (besides your knowledge) is your mental attitude. Don't quit, stay encouraged, and NEVER give up. Every potential deal that doesn't work gives you more street smarts and brings you a step closer to that next big beautiful deal.
Lastly, real estate is a neighborhood business. As a beginner, maybe concentrate on the area that you feel most comfortable with. Become an expert in that one area you choose, and speak to as many investors, agents, contractors, sellers, and even buyers as you can. You'll be amazed how leads will come from totally unexpected places.
Hope this helps you a bit. Looking forward to hearing about your first deal! Best of luck!
Keep evaluating markets. 3.5 years ago, just before pulling the trigger, I had airdna (market research tool) open on one tab and realtor on the other. On both websites I went up and down freeways, rivers, and coastlines to get a feel for the general pricing landscape for much the continental US on both the revenue and the acquisition side. Looked for markets where the annual revenue to home price ratio was as favorable as possible.
Shoot for 20%+, including rehab costs. Anything under 15% will have disappointing cash flow at best, especially if you are not self managing and/or have high HOA or property taxes. 5+ bedroom properties are more likely to hit those ratios than 2-3 bedrooms in most markets.
Hi Ryan, congrats for downsizing and creating financial flexibility, that’s definitely impressive.
You're right to question the numbers, a $600K property generating only $40K in annual revenue wouldn't come close to cash-flowing, especially after mortgage, taxes, insurance, utilities, and STR operating costs (cleaning, supplies, management, etc.
If you're flexible on location you should target more friendly markets. Explore emerging STR markets where purchase prices are lower, regulations are clear, and tourism or worker travel demand still supports solid occupancy. Think Midwest towns, college towns, or cities with medical hubs or event/attraction traffic.
Use tools like AirDNA or PriceLabs Market Dashboards to look at average daily rates, occupancy, and seasonality. Consider mid-terms rentals as well, (30-90+ day rentals) targeting travel nurses, consultants, or relocations. They’re often less competitive and more profitable than saturated Airbnb markets.
For good cash flow consider undervalued properties you can rehab, reposition, or convert to STR use legally. Lastly, talk to STR focused agents, property managers, and investors in the markets you're targeting.
I currently own and manage STR properties in Kissimmee, FL an ideal location thanks to its close proximity to Walt Disney World and other major attractions. What I love most is the lower stress level, as I typically rent to families and groups of friends on vacation. Property prices in this area generally range from $150K to $300K, depending on the exact location and amenities. In my experience, condos, townhomes, and smaller single-family homes perform best as STRs here. Their cozy layouts and access to resort-style amenities make them especially appealing to vacationing families.
If you have more questions and want to connect, feel free to reach out. But don’t give up!
Curious, what is the STR tax loophole? Have I missed something?
As to your question, real estate prices have climbed so high, so fast, and the fact that interest rates that have doubled in three years, means deals that cash flow with the usual 20 percent down are very hard to find. It might take 50 percent to get it done right now.
Curious, what is the STR tax loophole? Have I missed something?
As to your question, real estate prices have climbed so high, so fast, and the fact that interest rates that have doubled in three years, means deals that cash flow with the usual 20 percent down are very hard to find. It might take 50 percent to get it done right now.
STR "loophole" is section 469 that allows you to count the paper STR losses as active against losses your active W2 income. Much easier to fulfill the requirements than REPS or whatever other method is allowed for using LTR losses against W2 income.
I disagree with your 2nd paragraph, there are plenty of markets out there with homes well under the national median that still have strong visitor numbers. Mid-to-high end markets I would agree.
Hello Everyone - Newbie here(obivously). I'm trying to break into real estate. Money isn't an issue per se as we just downsized our primary so we have money from that. I get the 4 pillars and honestly the STR tax loophole is very appealing as I still have W2 income. BUT, for the life of me I cannot find any STRs that actually cashflow with a mortgage. For example the place will be $600K and generating say $40K in revenue?? Am I just doing it wrong? Any pointers would be awesome as I'm almost ready to just give up.
Is this not possible and I need to hope for the other 3 pillars to outweigh the lack of cashflow? I've looked in Frisco, CO, Traverse City, MI, Ellicottville, NY.
If a market is producing $40k of revenue on a $600k property, you need to look for a different STR market. That ratio would not be good on even an LTR market.
The last STR underwriting I did had a projected $110k revenue on a $500k property. Surprisingly, in the market of this STR this did not produce good cash flow but I suspect much better than $40k revenue on a $600k property.
Good luck
You're not doing anything wrong—this is a really common roadblock, especially with STRs in high-demand areas where property prices have outpaced revenue potential.
A few thoughts that might help:
Markets are tight right now: In many of the areas you mentioned (Frisco, Traverse City, Ellicottville), prices are high and a lot of the cash flow was already squeezed out during the STR boom of the past few years. You're not crazy—it's genuinely hard to find solid cash-flowing deals in these markets unless you're putting down a huge chunk or buying off-market.
Run the real numbers: A lot of STR revenue estimates floating around (like Zillow or AirDNA) are overly optimistic. Make sure you're calculating true net revenue after cleaning fees, management (even if you plan to self-manage), vacancy, platform fees, maintenance, insurance, and utilities.
Try mid-tier or emerging markets: Sometimes smaller vacation towns or regional drive-to locations that are just under the radar can still cash flow. Also look at areas with lenient regulations—tight local laws and permitting issues can kill a deal.
Focus on the STR tax strategy but don't force a bad deal: The tax benefits of the STR loophole (like bonus depreciation) can be huge, but if the property is bleeding money every month, it may not be worth it. Ideally, find one that gives you neutral to slightly positive cash flow, and let the tax strategy enhance your return.
Consider new build STRs or unique niches: Some investors are building purpose-built STRs (tiny homes, cabins, A-frames, etc.) in lower-cost markets and doing well due to a better cost-to-revenue ratio.
You're not alone in this—it’s just a tougher market to break into than it was a few years ago. Don’t give up, but you may need to adjust your market or deal criteria.
Don't let the (tax) tail wag the dog! The STR loop-hole is not a magic wealth creator, it just let's you write off STR losses IF you can show you qualify and in the end that probably translates to a few thousand dollars in tax savings. Not any kind of get-wealthy money. Instead, build your strategy around long term (decade+) goals.
@Ryan Berg Great question - you're not alone! In many markets, STR cash flow is tight with high prices and seasonality. Sometimes a great deal is off-market or needs creative structuring. Don't give up!
I am curious what market(s) you are looking at? It is still common in FL (at least Tampa) to get a 15% yield i.e. $90k gross on a $600k house. Cash on Cash return could be better depending on leveraging factors i.e. down payment, DSCR vs convention (APR differences), hiring management versus self management, etc.
The problem with the STR tax loophole is the current cash flow issue due to interest rates. The strategy I have found for exploiting the tax loophole is to acquire a multifamily property, such as a duplex, at a minimum.
Please take my advice with a grain of salt and consult a tax strategist or CPA before taking action. My friend's approach is to buy a duplex. Make one side an MTR and the other side an STR. He is cash flowing because his MTR covers a majority of the mortgage, and the STR side is just a bonus.
He leases each side of the property to his LLC. However, on the tax side, it appears that his one lease qualifies for the loophole due to the average stay being 7 days. I'll get further details on how this has worked out for him, but you may want to run this by a tax professional first.
Additionally, I'd recommend reaching out to Avery and Luke Carl if you're looking for a cash-flowing vacation rental, as this can also help you take advantage of the tax loophole.
The problem with the STR tax loophole is the current cash flow issue due to interest rates. The strategy I have found for exploiting the tax loophole is to acquire a multifamily property, such as a duplex, at a minimum.
Please take my advice with a grain of salt and consult a tax strategist or CPA before taking action. My friend's approach is to buy a duplex. Make one side an MTR and the other side an STR. He is cash flowing because his MTR covers a majority of the mortgage, and the STR side is just a bonus.
He leases each side of the property to his LLC. However, on the tax side, it appears that his one lease qualifies for the loophole due to the average stay being 7 days. I'll get further details on how this has worked out for him, but you may want to run this by a tax professional first.
Additionally, I'd recommend reaching out to Avery and Luke Carl if you're looking for a cash-flowing vacation rental, as this can also help you take advantage of the tax loophole.
Hi Ryan!
I am a Michigan native so I can help a bit with the TC properties you've looked at.
Biggest thing to find out / pay attention to, is if the city allows new STRs. Not just STRs in general but specifically new purchases to get a STR license. Traverse City as far as I know has a moratorium on STRs in the city, causing potentially the low income that you are seeing.
My 3 STRs are located in Boyne City (about 45 minutes away) and they do much better than I expected! If you want to talk about any "Up North" Michigan properties please feel free to reach out, I have some tips and tricks I'd love to share!
Hi! I completely understand your frustration because I have had a lot of clients here in San Antonio with the same concerns. We as a team have had a lot of success finding STRs in more centralized areas near the Airport and near the military bases. I feel like STRs have always been pretty successful here because we have a constant influx of tourists and people who visit San Antonio for a variety of reasons. I would look to see if you can find any data on the areas that you are looking into to buy to see which have been the most successful. Good luck!
I'm not a tax guy but I have been looking to Topsiders Condos down at Lake of the Ozarks, we stayed in a unit last summer and found that a lot of the units cash flow down at that complex. They are new so no issues you should have to worry about. I didn't do a deep dive yet, but I think this a great growing location you should look into.
Hey @Ryan Berg — totally get where you're coming from. You're not alone — we've talked to a lot of folks in the same spot: excited about the STR tax strategy but frustrated when the cash flow doesn't pencil out right away.
Out here in Boise, we've helped a bunch of investors run this play — and what we've found is that not every property is a good fit for this specific STR strategy. Especially in higher-cost vacation markets, the real win often comes from the tax strategy — using cost seg and accelerated depreciation to offset W2 income and build momentum for reinvesting.
How are you currently evaluating STRs — AirDNA, agent insights, or just raw listings? Are you working with anyone to break down land vs structure value? That can really impact how effective your depreciation strategy is. And bigger picture — are you wanting to own an STR because you're drawn to the hospitality/service side of the business, or is it mainly for the tax benefits and long-term equity growth?
Just curious and happy to chat more if it’s helpful.
In my local market of Gainesville, I have 400k properties generating 95k-100k in gross revenue. Clearwater Florida can generate 110k-140k on 600k properties and have seen equally impressive numbers in other states as well.
With the current STR market, being better than the competition is a must along with rethinking what makes a successful STR. There are so many battle tested and well known markets where some people are continuing to cash flow, and newbies are barely breaking even.
Having operators in your chosen market that own/manage SUCCESSFUL properties is a must.
I was able to take advantage of bonus depreciation when it was at 100% and 80%, and it was extremely beneficial for my finances and allowed me to roll tax savings into additional properties.
Hello Everyone - Newbie here(obivously). I'm trying to break into real estate. Money isn't an issue per se as we just downsized our primary so we have money from that. I get the 4 pillars and honestly the STR tax loophole is very appealing as I still have W2 income. BUT, for the life of me I cannot find any STRs that actually cashflow with a mortgage. For example the place will be $600K and generating say $40K in revenue?? Am I just doing it wrong? Any pointers would be awesome as I'm almost ready to just give up.
Is this not possible and I need to hope for the other 3 pillars to outweigh the lack of cashflow? I've looked in Frisco, CO, Traverse City, MI, Ellicottville, NY.
In this market “deals” are MADE, not found at “listed” price. In other words you need to NEGOTIATE to a price that allows profitability/cash flow, OR look for a property you can ADD VALUE to, OR, find a deal “off market”. As @Collin Hays said (he’s correct and to the point as he always is!) 20% down deals don’t cash flow positive at today’s ASKING prices and interest rates.
Ryan, what you’re running into is honestly really common. It’s not that the deals aren’t out there, it’s just that most people are using only part of the real data to evaluate them.
For instance, Airdna and Rabbu are fine as a starting point, but they almost always show only part of the bigger picture. And if you’re basing your decisions solely on that data, yea, it’s going to look like nothing cashflows. The reality is that those platforms don’t account for most of the nuanced factors that go into a successful listing.
Here's a quick example: I had a client looking for a 3 bed 2 bath in the Poconos. He kept seeing terrible revenue projections from Airdna and was close to looking at another market before he connected with me. I had to mention to him those numbers were based on everything including underperforming listings, properties with bad design, common amenities, and subpar pricing strategy. I knew from experience that the right 3 bed, in a popular HOA, set up correctly, could pull in over 60K+ a year. And that wasn't a guess. The rental management company I worked with had real comps proving exactly that.
He ended up moving forward with the right one. Same general layout as the others he was looking at, but it was done right and is seeing great success.
Point is, STR success -from my experience selling them- can be hyper local. You shouldn't just go off surface level data. If I were in your shoes I'd pair up with someone who can show you real numbers from actual listings in the market you want to be in.
Happy to talk through other examples if that helps. Just don’t give up yet. You’re not doing anything wrong. I confident, you just haven’t seen the right data yet.
Ryan, what you’re running into is honestly really common. It’s not that the deals aren’t out there, it’s just that most people are using only part of the real data to evaluate them.
For instance, Airdna and Rabbu are fine as a starting point, but they almost always show only part of the bigger picture. And if you’re basing your decisions solely on that data, yea, it’s going to look like nothing cashflows. The reality is that those platforms don’t account for most of the nuanced factors that go into a successful listing.
Here's a quick example: I had a client looking for a 3 bed 2 bath in the Poconos. He kept seeing terrible revenue projections from Airdna and was close to looking at another market before he connected with me. I had to mention to him those numbers were based on everything including underperforming listings, properties with bad design, common amenities, and subpar pricing strategy. I knew from experience that the right 3 bed, in a popular HOA, set up correctly, could pull in over 60K+ a year. And that wasn't a guess. The rental management company I worked with had real comps proving exactly that.
He ended up moving forward with the right one. Same general layout as the others he was looking at, but it was done right and is seeing great success.
Point is, STR success -from my experience selling them- can be hyper local. You shouldn't just go off surface level data. If I were in your shoes I'd pair up with someone who can show you real numbers from actual listings in the market you want to be in.
Happy to talk through other examples if that helps. Just don’t give up yet. You’re not doing anything wrong. I confident, you just haven’t seen the right data yet.
Hey! Those Poconos three bedroom, two bathroom homes that are pulling in 60+ K a year in revenue. How much are they netting in profits? My guess is hardly anything. Taxes are high, heating costs are very high, you’ve gotta pay a mortgage, you’ve gotta pay your helpers, supplies, insurance, repairs, etc etc etc.
I have friends who own houses in the Poconos and the annual expenses on a three bedroom two bath house tend to run around 50 or 60 K a year when you're STR-ing it, so they don't really wind up with any profit. Curious if you're seeing something different?
Ryan, what you’re running into is honestly really common. It’s not that the deals aren’t out there, it’s just that most people are using only part of the real data to evaluate them.
For instance, Airdna and Rabbu are fine as a starting point, but they almost always show only part of the bigger picture. And if you’re basing your decisions solely on that data, yea, it’s going to look like nothing cashflows. The reality is that those platforms don’t account for most of the nuanced factors that go into a successful listing.
Here's a quick example: I had a client looking for a 3 bed 2 bath in the Poconos. He kept seeing terrible revenue projections from Airdna and was close to looking at another market before he connected with me. I had to mention to him those numbers were based on everything including underperforming listings, properties with bad design, common amenities, and subpar pricing strategy. I knew from experience that the right 3 bed, in a popular HOA, set up correctly, could pull in over 60K+ a year. And that wasn't a guess. The rental management company I worked with had real comps proving exactly that.
He ended up moving forward with the right one. Same general layout as the others he was looking at, but it was done right and is seeing great success.
Point is, STR success -from my experience selling them- can be hyper local. You shouldn't just go off surface level data. If I were in your shoes I'd pair up with someone who can show you real numbers from actual listings in the market you want to be in.
Happy to talk through other examples if that helps. Just don’t give up yet. You’re not doing anything wrong. I confident, you just haven’t seen the right data yet.
Hey! Those Poconos three bedroom, two bathroom homes that are pulling in 60+ K a year in revenue. How much are they netting in profits? My guess is hardly anything. Taxes are high, heating costs are very high, you’ve gotta pay a mortgage, you’ve gotta pay your helpers, supplies, insurance, repairs, etc etc etc.
I have friends who own houses in the Poconos and the annual expenses on a three bedroom two bath house tend to run around 50 or 60 K a year when you're STR-ing it, so they don't really wind up with any profit. Curious if you're seeing something different?
The ones we manage are actually netting more than most 4+unit LTRs right now. Cant share specifics as you can understand. So your guess isn’t really accurate. But I do understand why it seems that way to you. You're generally right, that a lot of 3 beds out here don’t perform well. We're finding success marketing our 3's like a 2bed, giving us slightly lower ADR but an increase in occupancy because couples often travel more frequently here than familys. Also, myself and colleagues rarely advise our clients to go in full price or with no concession, so off the rip, we're working to make the deal make sense. Doesn't hurt that most our buyers have a decent rate.
If your friends are struggling, it might have more to do with internal factors: high rate, low down, inefficient pricing strategy, lack of design, or not keeping up with trends like saunas or outdoor setups. If it’s just a basic 3-bed with a hot tub and clunky layout, yeah, it’s going to underperform. Not saying that's your friends, but i agree that those^ types of homes fail before they begin.
Many STR markets are now saturated and experiencing dropping revenues.
So, investors have to be patient and research, research, research for the right "deal"!
Just a few years ago, you could close your eyes and buy almost anything and cashflow - those days are over.
You're asking a great question, and you're definitely NOT doing it wrong- the market for STRs has tightened a lot, and finding strong cash-flowing properties in popular, high-priced markets like Frisco, CO or Traverse City, MI is getting tougher, especially with today’s interest rates and elevated home prices.
That said, since you're still a W2 earner, you're in a powerful position to take advantage of one of the biggest real estate tax strategies available-cost segregation and bonus depreciation via the STR loophole.
You don’t need to keep the property in STR status forever to unlock the tax benefits.
The STR tax loophole (Material Participation Rule) only requires that you materially participate in the property during the first year when you take the bonus depreciation. Once that’s done and the write-off is captured, you can switch to long-term rental (LTR), use it personally, or even sell it later- all while keeping the tax deduction you took upfront.
So even if the cash flow is weak or slightly negative, the massive tax offset can make it worthwhile in year one, especially if you're earning strong W2 income and facing a high tax bill.
A few other thoughts:
Markets like Frisco and Traverse City have high acquisition prices that make cash flow tricky, but smaller vacation towns nearby may offer better ratios. Sometimes you can “zoom out” 20–30 minutes and find hidden gems.
Focus on breaking even or slight negative cash flow, but evaluate the total return picture: cash flow + appreciation + loan paydown + tax savings.
You can also house hack or rent it mid-term after the first year if needed to ease the holding cost.
Let the tax benefit carry the heavy load upfront, then pivot as needed. Happy to help you run numbers or review potential markets if you want a second set of eyes!
Best of luck,
Melissa
You're not doing it wrong — you're just looking in highly saturated, pricey markets where STRs rarely cash flow with a mortgage. Places like Frisco or Traverse City have high prices and competition, which crush ROI. Instead, look for under-the-radar spots within 1–3 hours of cities, where you can still buy for $300K–$400K and gross $40K–$60K with strong seasonal demand. Also, don't underestimate the STR tax loophole — even break-even deals can create massive tax wins if you materially participate. Cash flow is possible, but you'll need to pivot markets or add value creatively to make it work. Don't give up — just adjust your strategy.
Hey Ryan, It sounds like you're on the right track, but a few things may be affecting your cash flow. First, some STR markets like Frisco, CO, and Traverse City, MI, have high property costs, which can limit cash flow. Consider exploring more affordable markets like Cleveland, OH, where you can find properties with better cash flow potential. Ensure your revenue estimates are realistic aim for at least 1% of the property's purchase price in gross monthly revenue. Double-check the average nightly rates, occupancy, and seasonal trends in your target areas. Additionally, be mindful of high operating costs, including maintenance and management fees. If financing is affecting your cash flow, explore creative options like seller financing or partnerships. Lastly, while the STR tax loophole is appealing, it shouldn't be your only focus. Make sure your property is profitable based on strong revenue and expense management.
I’m Andrea Wilson, a real estate broker, mortgage loan officer, and investor based right here in Cleveland, Ohio. I’ve been in this game since 2007, and I work with everyone from first-time investors to seasoned pros looking to scale smart.
Cleveland is one of the best-kept secrets in real estate investing. Why? Low purchase prices, strong rental demand, and high cash flow potential. We’ve got stable job sectors like healthcare and education, a growing tech presence, and a ton of value-add properties that investors are scooping up and turning into cash machines.
I help investors do exactly that—find the right deals, structure the financing (yes, I do loans too), and connect with trusted contractors and property managers. Whether you’re local or investing from out of state, I’m a boots-on-the-ground resource who knows how to make deals pencil.
Price points are significantly lower in our market, offering excellent returns. I can share some opportunities with you to review, so you can get a feel if you like.