Exploring the idea of buying a STR

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Exploring the idea of buying a STR

Rodney Michels
Member since 2026 · 2 posts · 5 votes

I have interests in buying STR in Florida. Currently live in MN and have fears after buying, I will wish I didn't. Anyone out there have those same feelings but are happy they did it? Secondly, the financial burden of paying for the mortgage, maintenance and management of the place seems very stressful.

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G. Brian DavisPro Member
Investor · Hatboro, PA · Member since 2016 · 3k+ posts · 875 votes
3d

I'd be cautious with an out-of-state STR, especially if the numbers only work when occupancy and revenue stay high. You still have the mortgage, insurance, taxes, maintenance and management whether you have guests or not.

I’d run it with conservative revenue assumptions and make sure you’re comfortable carrying the property during slower periods. If it still works after that, then I’d take a serious look.

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  • Erik EstradaBusiness Member
    Lender · Member since 2022 · 6k+ posts · 1k+ votes
    3d

    Hey Rodney,

    Are you planning to live in the property? If the property is strictly for investment purposes, I would run the numbers as both an STR and LTR to help mitigate risk. In case the property does not work seasonally as an STR, you can pivot to an LTR.

    Does the property also work as a flip? This could also be a last resort if the project has a value-add opportunity.

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  • Nyisha Walton
    Lender · Houston, TX · Member since 2026 · 43 posts · 10 votes
    3d

    Rodney, it makes sense to price the financing and management costs before choosing a Florida market. For a short-term rental, I would compare the projected nightly revenue and occupancy with a conservative long-term-rent scenario, then confirm what income documentation a lender would use for the property. If you narrow your search to a property or county, I’d be glad to help you compare financing paths and estimate the cash needed, with no pressure.

    1Reply
  • Jules Aton
    MD/DC · Member since 2024 · 1k+ posts · 1k+ votes
    3d

    Hi, is the plan to use as vacation property for your family as well as STR? That seems to be the best case scenario for most STRs now because the value is in the experience moreso than strictly income. Florida can be tricky. The only place I'd consider is Tampa/St.Pete because I love the area and it should offer opportunities for STR, MTR and LTR allowing room to pivot if needed. Unfortunately its not as warm as I'd like in the winter. Our own @AndrewSteffans is a local expert who will hopefully weigh in on FL in general.

    As for the financial and emotional aspects if you have enough money that shouldn't be a regret or stress point. If you are on a constrained budget I wouldn't advise a STR in today's climate. Emotionally I have always purchased smart and convinced myself if I wasn't feeling it I could always re-sell, hopefully not at a loss but if so it is what it is. Best wishes with whatever you decide.

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  • G. Brian DavisPro Member
    Investor · Hatboro, PA · Member since 2016 · 3k+ posts · 875 votes
    3d

    I'd be cautious with an out-of-state STR, especially if the numbers only work when occupancy and revenue stay high. You still have the mortgage, insurance, taxes, maintenance and management whether you have guests or not.

    I’d run it with conservative revenue assumptions and make sure you’re comfortable carrying the property during slower periods. If it still works after that, then I’d take a serious look.

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  • Matthew Tregoning
    Property Manager · Melbourne, FL · Member since 2019 · 394 posts · 163 votes
    3d

    Before buying remotely, I would map the local response plan as carefully as the revenue. Who gets there for a lockout, who covers when the cleaner is sick, and who can check a repair before the next guest arrives? Ask any manager to walk you through those three situations with actual names and response times. That will make the operational risk much more concrete than a percentage fee alone.

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  • Rodney Michels
    OP
    Member since 2026 · 2 posts · 5 votes
    3d

    I really like all your responses. Thank You All for everything you said. Especially about, “what to do when the cleaner is sick!” These types of things never entered my mind. I think a place closer to home is the way I’ll go to start this off.

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  • Divin KanyamaBusiness Member
    Accountant · Seattle, WA · Member since 2025 · 525 posts · 221 votes
    3d

    @Rodney Michels Those concerns are completely reasonable—an out-of-state STR is both an investment and an operating business. Before buying, I'd run the numbers using conservative occupancy and nightly rates, then include management, cleaning, maintenance, utilities, furnishing, insurance, taxes, HOA fees, licensing, hurricane-related costs, and a healthy repair and vacancy reserve. Also confirm that local rules and the HOA allow short-term rentals and understand how easily those rules could change. A strong local manager, cleaner, handyman, and backup contacts are essential when you live in Minnesota. If the property only works under optimistic assumptions or the carrying costs would keep you up at night, passing is a valid decision. You might first rent in the target area, speak with local owners, or test a lower-risk market before committing. The best deal is one that still feels manageable during a slow season or an unexpected repair—not just one that looks good at peak occupancy.

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  • Mark Schilling
    Realtor · Lavallette, NJ · Member since 2026 · 3 posts · 2 votes
    2d

    I feel like it would depend on whether it was just an STR or not. If it didn't produce as much as you were hoping, would you still want to own it? Would you use it yourself and be able to carry it if it wasn't making much? That would tell me a lot.

    If you only like it because you think it can make money, then maybe pass. If you like the house and the rental income can help with some of the cost, then maybe it’s worth looking into.

    You also mentioned that you’re looking closer to home, so that may be an advantage while you’re learning the business.

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  • Matthew Tregoning
    Property Manager · Melbourne, FL · Member since 2019 · 394 posts · 163 votes
    2d

    Before choosing a market, I’d build the remote-ownership plan on paper: who can reach the property after hours, who verifies a turnover, and what happens if the air conditioning fails on a weekend. Then price those real quotes into a conservative month-by-month model, including a repair reserve and slower periods. A local manager interview can be useful even if you later decide to self-manage.

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  • J CastroBusiness Member
    Lender · Florida · Member since 2025 · 716 posts · 255 votes
    2d
    Quote from @Rodney Michels:

    I have interests in buying STR in Florida. Currently live in MN and have fears after buying, I will wish I didn't. Anyone out there have those same feelings but are happy they did it? Secondly, the financial burden of paying for the mortgage, maintenance and management of the place seems very stressful.

    Those are valid concerns, especially when investing out of state. The key is making sure the numbers work before buying and accounting for all expenses, including the mortgage, insurance, maintenance, property management, and seasonal vacancies.

    We help real estate investors explore financing options for investment properties, including short-term rental opportunities. Having the right financing and a realistic cash-flow analysis can make a big difference.


    Feel free to reach out if you'd like to discuss financing options for your Florida investment!

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  • Andrew SteffensBusiness Member
    Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
    2d

    I work with a lot of out of state buyers here in FL as a STR specializing buyers agent as well as a PM. Most of them have jitters and anxieties, I think its fairly normal. The key is working with a knowledgable agent, check and double check the numbers and data, and have a solid management plan in place.

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  • Rati Meskhishvili
    Tbilisi, Georgia (country) · Member since 2026 · 3 posts · 2 votes
    2d

    Hi Rodney,

    The stress you are describing is legitimate and can be put into numbers. It helps to work it out before you pick a market:

    Some costs come every month even without any guests . For example, a 350k place with 25% down payment at 6.75% interest is about 1.7k a month for the mortgage. Say property tax, insurance, and utilities add another 950 or so (insurance can run high in Florida). That's about 2,650 a month (or roughly 31.8k a year) whether anyone books or not.

    Now, lets work out what you keep per booked night:

    Say 250 a night all-in, 2.5 night average stays, a 150 cleaning cost per turnover and Airbnb's 15.5% fee:

    • With a manager at 20%, you keep about 109 a night - covering 31.8k takes about 290 booked nights (close to 80% of the year, and that's before any repairs).

    • Self-managed, you keep about 151 a night - so about 210 nights (around 58% of the year) to cover 31.8k.

    That's what people mean when they say the numbers only work at a high occupancy.

    Two things that should help with the fear:

    1. Use conservative revenue: get two estimates and go with the lower one. AirDNA's occupancy only counts nights the property was available, so take into consideration any nights you'd block for yourself.

    2. Keep about 6 months of those fixed costs in reserve on top of the down payment, about 16k in this example. If carrying that would be a stretch, the deal is too tight in my opinion, whatever the spreadsheet says.

    For running it yourself, going closer to home makes more sense to me, but do the same math there as well. The break-even doesn't change just because the property is nearer.

    (These are example numbers, so put in your own. I used AI to help check the math)

    1Reply
  • James Loffredo
    Lender · Dallas, TX · Member since 2024 · 10 posts · 3 votes
    2d

    Rodney, the fear is doing its job. Here’s how to answer it with numbers instead of nerves.

    Run the floor test. Take the full payment, PITI plus HOA plus management, and compare it to what the house rents for as a plain long-term rental. If it covers on long-term numbers, the STR income is the cherry on top and you'll sleep fine. If it only covers in peak season, that's the fear talking for a good reason. You never want to be playing catch-up every off-season.

    Two Florida-specific things. First, get the insurance quote early and get it exact. We’ve watched insurance kill deals in underwriting, especially on the larger, higher-value houses most STRs are. Second, Florida rents fell over the past year, so pull current rent data and don’t count on growth to rescue a thin deal.

    A house with no booking history usually gets sized on long-term rent anyway, so shop for houses that pencil that way. AirDNA gets used, but it’s gotten less reliable over time.

    The happiest people I work with ran the math at the worst case first. I run a lender, so take that into account.

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  • Adam Summerer
    Lender · Franklin, TN · Member since 2026 · 110 posts · 27 votes
    2d

    On the financing side, there are DSCR lenders that'll do STRs at up to about 80% LTV on a purchase and qualify off the projected short term rental income instead of your personal income, so it doesn't eat into your DTI. Tradeoff is a higher rate. If you'd really use it yourself part of the year, a second home loan can be 10% down at better pricing, but you can't count the rental income to qualify and it can't be run as a full time rental. Either way get a Florida insurance quote before you get attached to a property, that number can swing the math more than the rate.

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  • Jimmy LieuBusiness Member
    Real Estate Agent · Columbus, OH · Member since 2019 · 3k+ posts · 2k+ votes
    2d

    Welcome, Rodney. The regret worry is a healthy one, and the best way to deal with it is to buy the place only if it still works when it earns less than the projections say. Beyond the insurance and financing points above, two things trip up a lot of out-of-state STR buyers: Florida requires a state vacation rental license plus sales and tourist taxes, and many condo and HOA communities restrict or ban short stays, so confirm the rules for that exact address before you fall for a property. Also decide up front who runs it. A good local manager costs real money, but being 1,000 miles away with no one on the ground is usually what turns a manageable investment into a stressful one. For context, well-run STRs generally land around 15-20% cash-on-cash and tend to bring in roughly three times what the same house would as a long-term rental, but that only holds if the numbers work at purchase, so verify them on every deal. On our side, we run short-term rentals here in Columbus and it's been a really strong fit for us. What keeps it calm is a healthy cash reserve and a plan B, so a slow stretch can go mid-term or long-term instead of becoming a crisis. Happy to connect and compare notes.

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  • Kathy Weithman
    Real Estate Broker · Port Charlotte, FL · Member since 2026 · 3 posts · 0 votes
    1d

    I would want to know how hands-on you want to be. If you’re feeling like you need to be there for every repair, then maybe start local. Once you know what you’re getting yourself into, you can always branch out.

    Another thing to look at is how much work the home will need. Having to manage a home that needs a lot of work from another state could become stressful. If I ever wanted to invest in Florida, I would look for a property I felt comfortable owning and maintaining from a distance.

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  • Karen CubberleyBusiness Member
    Realtor · Sevierville, TN · Member since 2026 · 18 posts · 1 vote
    1d

    Those feelings are completely understandable, especially when you're considering buying an out-of-state STR! Buying an investment property is a big financial commitment, and the last thing you want is to feel like you've made the wrong decision.

    As an STR owner and investment specialist here in the Smoky Mountains, I always tell investors that the numbers need to make sense before emotions enter the picture. It's important to understand not just potential rental revenue, but also mortgage payments, management fees, maintenance, insurance, taxes, and unexpected expenses.

    One of the biggest questions I encourage investors to ask is: If rental revenue drops 10–20%, can I still comfortably carry this property?

    Having a reliable local team and a realistic operating budget can make a tremendous difference, especially when investing from another state.

    My advice? Don't let fear stop you, but don't let excitement override the numbers either. The right investment should fit your financial goals and your comfort level with risk. And remember, sometimes the best investment decision is knowing when to walk away.

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  • Deborah Wodell
    Lender · Sanford, NC · Member since 2024 · 358 posts · 120 votes
    1d

    Those are valid concerns. From a lender’s perspective, I’d recommend running the numbers conservatively and making sure you have enough reserves to cover vacancies, maintenance, and unexpected expenses before taking the plunge.

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  • Onn Biri
    Miami, FL · Member since 2025 · 1 post · 0 votes
    1d

    Rodney, starting closer to home is a reasonable call, and the questions you're asking will carry over wherever you buy. If Florida comes back on the table later, here are a few Florida-specific things that rarely show up in a spreadsheet.

    First, the building or HOA often decides more than the city does. Many condos and communities set minimum stays or limit rentals, so get the written rules for the exact unit before you get attached. In Florida, a newer condo rental limit usually binds only owners who voted for it or bought after it passed, so check when the rule was adopted.

    Second, hurricane season (June to November) is an operating cost, not just an insurance line. Someone has to prepare the property before a storm, check it after, and deal with cancellations in between.

    Third, AC is a guest emergency here. Budget for a service contract and a tech who answers on weekends.

    Finally, the slow season varies a lot by town. Ask local owners which months are actually quiet where you're looking, then test whether you can carry those months comfortably.

    Disclosure: I run a vacation-rental management company in South Florida.

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