New Member/Investor Intro in MA

[Will Rockwell]

Hi, everyone- excited to join the community! 

I’m 29 YO and grew up on the North Shore of MA and will be moving back to the Boston/North Shore region this year. I’m beginning the process of building a small, long-term rental portfolio and I’m in the learning/relationship-building phase before pursuing my first deal.

After doing some research and soul-searching, my tentative plan is to house hack a 2-family within the next 12–24 months and hold it long term, with the goal of gradually building a portfolio of 3–4 properties over the next 10–15 years. I work full time and view this primarily as a long-term wealth and financial-independence strategy rather than a quick cash-flow play. I’m focused on strong locations and fundamentals, but also trying to be disciplined about numbers and timeline to break even.

Right now I’m mostly trying to validate my buy box (i.e., are my goals reasonable?), learn how other local investors are viewing the current MA market, understand which North Shore / near-Boston areas people still feel make sense for small multifamily, and connect with people who’ve bought their first property in the last few years and are managing it alongside a full-time job

If anyone here invests in the North Shore, Greater Boston, or nearby markets and is open to sharing perspective (even briefly), I’d love to connect and learn from your experience. Not looking for deals or partnerships at this stage. Just trying to build a realistic understanding of the market and how others are approaching it right now.

Appreciate any advice, and looking forward to learning from the community!

-Will

** I also posted this in the "Starting Out" Category since it also seemed pertinent. My apologies if "double dipping" in multiple categories isn't the right approach.**