Long time accidental real estate investory

Long time accidental real estate investory

Investor · Bow, NH · Member since 2025 · 2 posts · 3 votes

I've owned additional properties and been "buy and hold" for some time without a real strategy other than "I like this place, and would like to come here myself" but without a financial strategy or playbook.   

I'm looking to pivot with purpose, and build a team to help me make a more robust real estate portfolio to help me accelerate through and into retirement.  

I'm located near Manchester, NH, but interested in investing in many places in New England. I think one of the first things I'd like to get is help with a local recommendation on a lawyer to help me structure a trust and perhaps LLC to protect my family and assets as I continue to invest.

I'm really interested in learning more about how people are seeing certain markets, approach their strategy and getting more focused myself, as I work to sell my first property to free up some capital and turn it into more productive capital.

Feel free to send me any recommendations or ideas you have!

Thanks!

Chris

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Aaron ZimmermanBusiness Member
Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
1y

I'm based in Chicago and see a lot of real estate transactions through the eyes of my clients. I'd say many of them are either trying to buy deeper, focus on larger value add or house hacking. All of these strategies can work but it comes down to having the right team. 

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  • New to Real Estate · Miami, FL · Member since 2024 · 1k+ posts · 479 votes
    1y

    Welcome, Chris! You’re making a smart shift, from passive holding to purposeful investing. Selling to redeploy capital and setting up the right legal structure is a strong foundation for scaling. New England has solid markets, and with your experience, you’re in a great spot to grow with focus.

    Happy to chat if you want to dive deeper.

  • Terrance HillPro Member
    Realtor · Memphis, TN · Member since 2010 · 425 posts · 117 votes
    1y

    Welcome Chris! Sounds like you’ve already built a solid foundation and now you’re just looking to take it to the next level with more strategy and structure. In NH/NE, having a solid RE attorney who understands entity structuring and estate planning will be a huge asset — a lot of investors here recommend asking your CPA for referrals since they often work closely with attorneys.

    As for pivoting with purpose, many investors in your shoes start by clarifying whether they want to optimize for cash flow, appreciation, or lifestyle flexibility — that decision usually shapes whether they lean toward multifamily, short-term rentals, or commercial.

    • Investor · Bow, NH · Member since 2025 · 2 posts · 3 votes
      1y
      Quote from @Terrance Hill:

      Welcome Chris! Sounds like you’ve already built a solid foundation and now you’re just looking to take it to the next level with more strategy and structure. In NH/NE, having a solid RE attorney who understands entity structuring and estate planning will be a huge asset — a lot of investors here recommend asking your CPA for referrals since they often work closely with attorneys.

      As for pivoting with purpose, many investors in your shoes start by clarifying whether they want to optimize for cash flow, appreciation, or lifestyle flexibility — that decision usually shapes whether they lean toward multifamily, short-term rentals, or commercial.

      Thanks!   Yes, I think the property we have in Rangeley will remain a lifestyle flex focused property, i think we will probably look for a combo of flips to build some more capital and cash flow favorable rentals to build on our cash flow.
  • Aaron ZimmermanBusiness Member
    Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
    1y

    I'm based in Chicago and see a lot of real estate transactions through the eyes of my clients. I'd say many of them are either trying to buy deeper, focus on larger value add or house hacking. All of these strategies can work but it comes down to having the right team. 

  • Member since 2025 · 7 posts · 4 votes
    11mo

    Hi Chris, sounds like you have a great start, even if it was with properties you just like! Investing in real estate is never a bad thing, especially if it is something you see value in. I live near Concord, I’m trying to start my own portfolio. I’ve done live in flips, new manufactured homes, and a full gut renovation with my husband. If you’re ever interested in meeting up, don’t hesitate to reach out! I am a realtor as well, so you can find me on Facebook and Instagram. Have a great night! 

  • Investor · NH · Member since 2018 · 36 posts · 21 votes
    11mo

    Hi Chris! I'm an investor-focused agent in Manchester with the Candor Investment Group. I just went through my first 1031 into a larger deal and am under contract on another 15 units. Our group has tons of resources / connections with our mission of helping 1 million people reach financial independence. I'd love to help you out where I can! 

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