New Member Looking for Southwest Florida Connections

New Member Looking for Southwest Florida Connections

New to Real Estate · Naples, FL · Member since 2026 · 3 posts · 5 votes

Hi everyone, I’m Geoff. My real estate experience began with buying my first home, renovating it, and later selling it for roughly twice the original purchase price. That experience sparked my interest in finding additional investment opportunities and learning more about real estate investing.

I’m currently interested in fix-and-flip projects, long-term rental properties, and commercial real estate. I’m looking to connect with local investors, contractors, agents, lenders, and other experienced professionals who are willing to share their knowledge. I’m especially interested in learning how others evaluate deals, manage renovations, finance properties, and identify opportunities in the local market.

My long-term goal is to build enough experience and income through real estate to eventually transition out of my current career and invest full time. I look forward to meeting people in the Naples and Southwest Florida area, learning from the community, and contributing what I learn along the way.

5Reply
483 views

Most Popular Reply

Investor · Washington, DC · Member since 2022 · 122 posts · 147 votes
1mo

Welcome to the community Geoff! A bunch of us will be in your area for our annual conference beginning of October (BPCON Orlando 10/2-4). Let me know if you have any questions about it--hopefully you can join us!

See this reply in the discussion

19 Replies

Jump to latestLatest
  • Steven GlickBusiness Member
    Lender · Buffalo · Member since 2024 · 115 posts · 33 votes
    1mo

    Welcome to BP, Geoff. Doubling your money on your first home is a great way to catch the investing bug.

    Since you're exploring flips, rentals, and commercial, I'd spend some time narrowing your focus first. Each strategy has a different financing structure, timeline, and risk profile, so getting clear on that early makes evaluating deals much easier.

    One thing I'd definitely factor into your underwriting in Southwest Florida is insurance. It's become a much bigger line item over the past few years, and it can materially change a deal's cash flow or flip margins.

  • Bill HamptonBusiness Member
    Accredited Investment Fiduciary, AIF®, Financial Planner, Tax Strategist, Real Estate Investor · Atlanta, GA · Member since 2012 · 2k+ posts · 977 votes
    1mo

    Welcome to Bigger Pockets. Check out your local real estate investors association for networking and education. 

    Good luck investing. 

    Hampton Tax and Financial Services LLC4.7106 Reviews
  • Ashish AcharyaBusiness Member
    CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
    1mo

    Geoff, welcome to BiggerPockets. You already have a useful advantage because you’ve gone through a renovation and sale before, so you understand that a lot of the profit is made in the planning and execution, not just at closing.

    Since you’re looking at fix-and-flips, long-term rentals, and commercial properties, I’d avoid trying to learn all three at once. Pick one strategy first, define a clear buy box, and start building relationships with local agents, lenders, contractors, insurance professionals, and property managers who already work with investors.

    I’m from Florida as well, so I’m well aware of how insurance costs, property taxes, flood exposure, permitting, and renovation timelines can affect deals here. In Naples and Southwest Florida, those items need to be part of the underwriting from day one.

    I’d also think about the tax structure before the first purchase. If you end up doing flips regularly, an S-Corp may be worth evaluating because flipping is generally an active business rather than passive rental activity. If you go the rental route, I’d look at depreciation and whether a cost segregation study makes sense once the property is placed in service. Depending on the property and your tax situation, cost seg can accelerate depreciation and improve the early-year after-tax return.

    The structure should really match the strategy you choose rather than trying to use one entity for everything.

    Happy to connect!

    INVESTOR FRIENDLY CPA®5241 Reviews
    TaxMD® | AI-Powered Tax Planning
  • Solo 401k Expert · Anaheim Hills, CA · Member since 2012 · 18k+ posts · 6k+ votes
    1mo

    Welcome to the BP community, Geoff! We're glad you joined us.

    Set up keyword alerts to be notified of the topics that interest you: http://www.biggerpockets.com/alerts

    Good luck on everything!

  • Arman AhmedPro Member
    Real Estate Agent · Columbus Cleveland Dayton, OH · Member since 2024 · 2k+ posts · 923 votes
    1mo
    Quote from @Geoff Todd:

    Hi everyone, I’m Geoff. My real estate experience began with buying my first home, renovating it, and later selling it for roughly twice the original purchase price. That experience sparked my interest in finding additional investment opportunities and learning more about real estate investing.

    I’m currently interested in fix-and-flip projects, long-term rental properties, and commercial real estate. I’m looking to connect with local investors, contractors, agents, lenders, and other experienced professionals who are willing to share their knowledge. I’m especially interested in learning how others evaluate deals, manage renovations, finance properties, and identify opportunities in the local market.

    My long-term goal is to build enough experience and income through real estate to eventually transition out of my current career and invest full time. I look forward to meeting people in the Naples and Southwest Florida area, learning from the community, and contributing what I learn along the way.


    You’ve already got a great start with that first renovation and sale. I’d focus on getting really comfortable with deal analysis, rehab numbers, and financing before trying to tackle everything at once. Build relationships with contractors, agents, lenders, and investors as you go. And if you’re open to investing outside Southwest Florida, Midwest markets are worth exploring for more affordable entry points and value-add opportunities.

  • Lender · Tampa/Saint Petersburg, FL · Member since 2014 · 356 posts · 148 votes
    1mo

    Welcome Geoff! I’m over on the lending side and work with a lot of investors/house hackers. My husband is a realtor who mainly works with investors too, so we’re constantly talking deals from both the financing and acquisition side.

    SW Florida definitely has opportunities, but financing can make or break a deal, especially once you start getting into rentals and flips. Happy to be a resource if you ever want to bounce around financing options or numbers on a deal. My sister in law is also a realtor there if you need a solid connection.  

    • New to Real Estate · Naples, FL · Member since 2026 · 3 posts · 5 votes
      1mo
      Quote from @Amber Stout:

      Welcome Geoff! I’m over on the lending side and work with a lot of investors/house hackers. My husband is a realtor who mainly works with investors too, so we’re constantly talking deals from both the financing and acquisition side.

      SW Florida definitely has opportunities, but financing can make or break a deal, especially once you start getting into rentals and flips. Happy to be a resource if you ever want to bounce around financing options or numbers on a deal. My sister in law is also a realtor there if you need a solid connection.  


       Hi Amber, thanks for reaching out. I really like the St. Pete area and have watched that area explode over the years. I've always kicked myself for not jumping into that market because I saw it changing ~ 15 years ago.

  • Todd AndersonPro Member
    Real Estate Agent · Cape Coral, FL · Member since 2023 · 392 posts · 175 votes
    1mo

    @Geoff Todd,

    Good to meet you. Welcome to REI in SW Florida, and congrats on your first deal going well.

    The best way to make connections is to go to the SW Florida REIA. the have meeting 2 times a month. It is run by some very knowledgeable people. I think you will enjoy the networking.

    I moved to the area 3 years ago and have no regrets.  I have been investing for over 30 years so it just made sense to get licenced here. It has been interesting to come to this market at this time to see how this market changes.  

    If you would like to connect I can give you some info on the REIA or help answer any questions you might have.

    Best of luck

    • New to Real Estate · Naples, FL · Member since 2026 · 3 posts · 5 votes
      1mo
      Quote from @Todd Anderson:

      @Geoff Todd,

      Good to meet you. Welcome to REI in SW Florida, and congrats on your first deal going well.

      The best way to make connections is to go to the SW Florida REIA. the have meeting 2 times a month. It is run by some very knowledgeable people. I think you will enjoy the networking.

      I moved to the area 3 years ago and have no regrets.  I have been investing for over 30 years so it just made sense to get licenced here. It has been interesting to come to this market at this time to see how this market changes.  

      If you would like to connect I can give you some info on the REIA or help answer any questions you might have.

      Best of luck


       Hi Todd. I just discovered the SWFL REIAs last week. I will be looking into some of these events going forward. 

  • Real Estate Broker · TX · Member since 2026 · 3 posts · 1 vote
    1mo

    Thats amazing! If you need financial planning for your next deal, just let me know here

  • J CastroBusiness Member
    Lender · Florida · Member since 2025 · 684 posts · 242 votes
    1mo

    Hi @Geoff Todd, welcome to BP!
    Your first renovation and sale sounds like a great foundation to build on. The fact that you're looking to learn the deal analysis, renovation, financing, and market sides of the business is exactly the right approach.

    As you start looking at opportunities, one of the biggest things I'd recommend is learning to analyze the deal before getting emotionally attached to the property. Know your acquisition cost, realistic rehab budget, ARV, holding costs, financing costs, and exit strategy before submitting an offer.

    You're also in a great position by actively building relationships with contractors, Realtors, investors, and lenders. Those connections can become one of your biggest advantages as you transition toward investing full time.

    Welcome aboard, and best of luck building your Southwest Florida network. Feel free to connect—I’d be happy to be a resource as you evaluate potential deals.

    JCREIG Capital Funding
  • Ismael ReyesPro Member
    Rental Property Investor · Port St. Lucie · Member since 2013 · 138 posts · 96 votes
    1mo
    Quote from @Geoff Todd:

    Hi everyone, I’m Geoff. My real estate experience began with buying my first home, renovating it, and later selling it for roughly twice the original purchase price. That experience sparked my interest in finding additional investment opportunities and learning more about real estate investing.

    I’m currently interested in fix-and-flip projects, long-term rental properties, and commercial real estate. I’m looking to connect with local investors, contractors, agents, lenders, and other experienced professionals who are willing to share their knowledge. I’m especially interested in learning how others evaluate deals, manage renovations, finance properties, and identify opportunities in the local market.

    My long-term goal is to build enough experience and income through real estate to eventually transition out of my current career and invest full time. I look forward to meeting people in the Naples and Southwest Florida area, learning from the community, and contributing what I learn along the way.

    Welcome, Geoff. That first renovation and sale is a great intro to this business. Doubling your money on your own home will do more to convince you real estate works than any book or podcast could.


    Fix and flip, rentals, and commercial is a wide range to explore, but there's nothing wrong with casting a broad net early on while you figure out what fits your strengths and goals. Connecting with local contractors, lenders, and agents in Southwest Florida will teach you more about evaluating deals and managing renovations than almost anything else you could do right now.


    Your long term goal of transitioning out of your current career is a strong one to build toward. Keep showing up, keep asking questions, and you'll get there. Welcome to the community.



  • Adam BartomeoBusiness Member
    Real Estate Broker · Cape Coral, FL · Member since 2015 · 2k+ posts · 1k+ votes
    1mo

    Welcome to BP and SWFL! I only know of one investor that is flipping right now. Due to local market conditions, it is very difficult to flip properties. Personally, I am buying and holding. Purchase prices are very low right now and if you just hold for a while you should make a killing.

  • Investor · Washington, DC · Member since 2022 · 122 posts · 147 votes
    1mo

    Welcome to the community Geoff! A bunch of us will be in your area for our annual conference beginning of October (BPCON Orlando 10/2-4). Let me know if you have any questions about it--hopefully you can join us!

  • Real Estate Agent · Tampa, FL · Member since 2026 · 1 post · 0 votes
    1mo

    Welcome to the community Geoff! I'm an agent here in Tampa and I work for an investment brokerage! We cover a 2/2.5 hour radius of Tampa, I would love to connect to tell you a little about my brokerage and how you can get some eyes on our properties! 

  • Brad SeidBusiness Member
    Lender · Licensed in 28 States · Member since 2026 · 141 posts · 40 votes
    1mo

    @Geoff Todd Great story, Geoff! As you explore fix-and-flips, rentals, and commercial deals, having the right financing partner can make a big difference. I help investors with funding options for their real estate projects. Happy to connect and see if I can help with your next deal!

  • Jorge VazquezBusiness Member
    Real Estate Broker · Tampa, FL · Member since 2017 · 1k+ posts · 684 votes
    1mo

    Geoff, welcome! Sounds like you already got a great introduction to real estate with that first renovation. I’ve been investing in Florida for over 20 years and my biggest advice is keep it simple, learn how to run the numbers really well, and focus on buying right. The market is different today, but there are still plenty of opportunities if you’re patient and don’t force a deal. I’m a big fan of rentals and creating equity from day one instead of depending on appreciation. Happy to connect anytime and talk real estate.

    Graystone Investment Group4.6271 Reviews
  • Member since 2023 · 19 posts · 9 votes
    1mo

    Hey Geoff,

    Welcome to the BP community and congrats on the sale of your home! I am also in the Naples area, recently moved up from Miami. Definitely a lot of opportunity in the SWFL area, whether that be through rentals or through flipping. Personally I am more focused on the buy and hold strategy, specifically with small multi-family properties. I am currently selling some properties in Tallahassee, FL and investing in 2-4 units in Lehigh Acres.

    However I can tell you that there is certainly flip opportunities, even here in Naples. When I was searching for my own primary residences most of the homes I ended up looking at were flips, including the home I ended up choosing. Doing some due diligence it usually seemed to be regarding the aging population and residences ending up in the possession of relatives/children who are just looking to offload.

    I also recently started looking into the SWFL REIA meetings, hopefully see you there one day. Would love to connect and hear about which strategy you ultimately choose. Best of luck!

Join the conversationCreate a free account to reply, vote on answers and follow this thread.