New to Real estate. grateful for any advice and guidance!!!
Good morning everyone,
I’m pretty new to Real Estate investing, based around MA / Northern CT near East Longmeadow. Just looking to connect with people who are actually out there buying and thinking long term. I want to diversify from purely equities into Real estate.
Right now I’m renting a 3-bedroom for about $2,500, so I’ve been trying to figure out what makes the most sense next and whether to house hack or go straight into an investment if the numbers are better.
I’m also a dad of four and a physician, with a background in programming, and I’ve been trying to build better systems (especially using AI) to get more consistent with analyzing deals. I could definitely use some help refining my buy box and improving how I identify good opportunities.
Lately I’ve just been looking at 2 to 4 unit deals pretty much every day. Like nothing fancy, just Zillow and Redfin and trying to get a feel for what’s actually a good deal vs not.
Trying to get a better handle on a few things:
• What do you actually care about when looking at deals? What really matters vs what doesn’t
• How your buy box changed over time compared to when you started
• How you quickly screen deals without going down a rabbit hole every time which can happen every day as this is such a intellectually fascinating space for me!
Also, if anyone is local and actively investing in MA or CT, would be great to connect. As my main purpose is to build great relationships and with time and effort gain some minor level of competence. This is what truly drive me good people and great learning. Ofcourse, generating some extra funds to take the kids on fun trips can never hurt also.
Appreciate any thoughts as I am just trying to stay consistent and not overthink it too much.
Gratefully,
Martand
Most Popular Reply
You’re in a great spot, especially with your analytical background. The key now is simplifying what actually matters so you don’t get stuck overanalyzing every deal. Most investors focus on a few core things first: purchase price vs rent, realistic expenses, and whether there’s enough margin for things to go wrong, then only go deeper if it passes that quick filter. Your buy box will tighten over time, but early on it’s about reps and pattern recognition more than perfection. In higher-cost areas like MA/CT, a lot of people find it harder to hit strong cash flow, which is why many also explore out-of-state options in Midwest markets where 2–4 units can make the numbers work more easily while you’re learning. Stay consistent like you are, just don’t let the analysis slow down your ability to eventually take action.