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 · 3 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 · 871 votes
6h

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
    7h

    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 · 35 posts · 9 votes
    7h

    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
    7h

    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 · 871 votes
    6h

    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.

    2Reply
    • J CastroBusiness Member
      Lender · Florida · Member since 2025 · 709 posts · 254 votes
      20m
      Quote from @G. Brian Davis:

      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.

      Those are valid concerns, especially when investing out of state. At JCREIG Capital Funding, we work with real estate investors looking to finance investment properties, including short-term rental opportunities. The key is making sure the numbers work before you buy. I’d recommend running the numbers conservatively, accounting for mortgage payments, maintenance, insurance, property management, and slower rental seasons. Feel free to reach out if you’d like to explore financing options and see what might make sense for your investment goals!

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  • Matthew Tregoning
    Property Manager · Melbourne, FL · Member since 2019 · 373 posts · 157 votes
    4h

    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.

    1Reply
  • Rodney Michels
    OP
    Member since 2026 · 2 posts · 3 votes
    3h

    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.

    1Reply
  • Divin KanyamaBusiness Member
    Accountant · Seattle, WA · Member since 2025 · 481 posts · 198 votes
    1h

    @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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