Florida Vacation Rental Manager Looking to Connect and Contribute

Florida Vacation Rental Manager Looking to Connect and Contribute

Property Manager · Saint Petersburg · Member since 2026 · 7 posts · 2 votes

Hey everyone, I’m Scott Dinan. I’m a husband, father of three, and the founder of TrustFirst Management, a full-service vacation rental management company here in Florida.

We primarily manage short-term rentals throughout the Tampa Bay area, including Saint Petersburg, Indian Rocks Beach, Anna Maria Island, Bradenton Beach, Bradenton/Sarasota, and the surrounding Gulf Coast markets. Over the years, our team has managed more than 50 properties, ranging from smaller condos to large luxury waterfront homes.

I originally got into this business because I saw vacation rentals as a way to build long-term freedom for my family. Along the way, I’ve really come to love the combination of real estate, hospitality, revenue management, property positioning, and building systems that create better results for both owners and guests.

One part of the business I especially enjoy is helping agents, investors, and their clients evaluate potential vacation rentals. I regularly create detailed pro formas that cover projected revenue, operating expenses, local regulations, property positioning, and potential opportunities to improve performance.

I’m not a licensed real estate agent, so I don’t represent buyers or sellers. My role is to provide the vacation rental underwriting and operational perspective. When an agent sends me a property to evaluate, I fully respect that relationship and work alongside them to help their client make a more informed decision.

I joined BiggerPockets to continue learning, contribute wherever my experience can be helpful, and connect with investors and agents who are active in the Florida market. I’m especially interested in conversations around short-term rental acquisitions, underwriting, management, and scaling a hospitality business.

If you’re evaluating a vacation rental in one of our markets or ever want another set of eyes on a deal, I’m always happy to connect and help however I can.

Looking forward to getting to know everyone!

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  • Allie H.Pro Member
    Director of Program Management and IT Services at BiggerPockets · Denver, CO · Member since 2017 · 3 posts · 1 vote
    1mo

    Welcome to BiggerPockets, Scott! Glad to have you here, and thanks for offering to share your experience with folks evaluating deals in the Florida market. Your reason for getting into this (to building more freedom for your family) is the same "why" a lot of us share, so you're in good company.

    In case you hadn't heard, our conference is in Orlando this year in October. The whole BP team will be there and we'd love to meet you in person if you can make it! It's a great place to make in-person connections, learn from others, and share your expertise. If you decide to come, feel free to use my code ALLIE100 for $100 off (and PS - early bird pricing ends July 31st).

    BiggerPockets
    • Property Manager · Saint Petersburg · Member since 2026 · 7 posts · 2 votes
      1mo
      Quote from @Allie H.:

      Welcome to BiggerPockets, Scott! Glad to have you here, and thanks for offering to share your experience with folks evaluating deals in the Florida market. Your reason for getting into this (to building more freedom for your family) is the same "why" a lot of us share, so you're in good company.

      In case you hadn't heard, our conference is in Orlando this year in October. The whole BP team will be there and we'd love to meet you in person if you can make it! It's a great place to make in-person connections, learn from others, and share your expertise. If you decide to come, feel free to use my code ALLIE100 for $100 off (and PS - early bird pricing ends July 31st).


       Sounds good, thanks for sharing!

  • Jorge VazquezBusiness Member
    Real Estate Broker · Tampa, FL · Member since 2017 · 1k+ posts · 676 votes
    1mo

    Very nice to meet you, Scott! We manage more than 500 properties across the Tampa Bay area, including both long-term and short-term rentals. It sounds like we share many of the same interests, especially underwriting, property management, and helping investors make better decisions.

    I would love to connect, exchange ideas, and explore ways we may be able to support one another. Welcome to the community!

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    • Property Manager · Saint Petersburg · Member since 2026 · 7 posts · 2 votes
      1mo
      Quote from @Jorge Vazquez:

      Very nice to meet you, Scott! We manage more than 500 properties across the Tampa Bay area, including both long-term and short-term rentals. It sounds like we share many of the same interests, especially underwriting, property management, and helping investors make better decisions.

      I would love to connect, exchange ideas, and explore ways we may be able to support one another. Welcome to the community!

      Impressive stuff! Yes, I'd love to connect. I get many inquiries for long-term rental management. We'd love to have a referral partner!
  • Lender · Tampa/Saint Petersburg, FL · Member since 2014 · 355 posts · 146 votes
    1mo

    Welcome, Scott! Sounds like you've built a great niche. I work with a lot of investors buying STRs in Florida, and having someone who can provide realistic underwriting / operational insight before they buy is a HUGE asset. I personally am a mortgage broker and also work with lenders that can qualify borrowers using AirDNA projections, so we're often having those same conversations upfront. Looking forward to seeing you around BP!

    • Property Manager · Saint Petersburg · Member since 2026 · 7 posts · 2 votes
      1mo
      Quote from @Amber Stout:

      Welcome, Scott! Sounds like you've built a great niche. I work with a lot of investors buying STRs in Florida, and having someone who can provide realistic underwriting / operational insight before they buy is a HUGE asset. I personally am a mortgage broker and also work with lenders that can qualify borrowers using AirDNA projections, so we're often having those same conversations upfront. Looking forward to seeing you around BP!

      Thanks for the warm welcome, Amber! I just sent you a message. Would love to connect soon!
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