New to Real estate. grateful for any advice and guidance!!!

Real Estate Agent · Columbus Cleveland Dayton, OH · Member since 2024 · 2k+ posts · 968 votes

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

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.

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Amit PatelBusiness Member

Property Manager · Bartlett, IL · Member since 2025 · 170 posts · 67 votes

6mo

Hi Martand!

Congrats on diving into real estate! It is a smart move diversifying as a busy dad and physician. I’m the owner at PM in the Chicago suburbs.

Quick advice for MA/Northern CT: Start with house hacking a 2-4 unit. You’re already paying $2,500 rent — living in one side while the others cover most of the mortgage is still the easiest low-risk entry.

What actually matters on deals:

Strong cash flow after realistic expenses (budget 8–10% of price for CapEx)

Good location + rental demand

Roof, mechanicals, and sewer condition

Price-to-rent ratio (aim for 1% rule or better)

Everything else is secondary.

Fast screening hack: Price ÷ rent, check comps, quick drive-by or Street View. If it passes, then dig deeper.

Hope this helps! Stay consistent.

Good luck in this!

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Ken M.

Investor · Get yourself trained before doing something inadvisable. · Member since 2024 · 3k+ posts · 1k+ votes

6mo

Quote from @Martand Chhibber:

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

I don't think there is a way to program for the inconsistencies of real estate. It needs to be learned from the ground up.

0 Reply

Martand Chhibber

OP

Member since 2026 · 3 posts · 3 votes

6mo

Thank you for your replies Arman, Amit and Ken!

As I type this at 4 am! I keep coming back to my old car from residency. Much like the properties that are over a 100 years old out here in MA/CT. At first look it does not pass the test. It’s definitely a “value add” for sure, LOL.

However, like a old shoe, I deeply understand it. I know every dent and scratch as I was there for all of it during the past 15 yrs that I have owned it.

This is why, experience especially the human part of it so powerful. We are able to extrapolate things that most people may overlook in an old car or an older part of town where a gem of a deal may hide.

This is what AI still cannot do yet. It may know what’s happening in 123 Main Street but all the intricacies of side street A through Z still elude it. This is why hallucinations or inaccuracies are a real thing in LLM’s (Large Language Models).

So forums such as these are so powerful as we are able to share our collective experiences to learn and grow while helping enhance our own buy boxes!

For me the ability to apply seemingly unrelated principles from different fields to generate a solution is very fulfilling. Very similar to the different backgrounds represented in a forum can collectively provide a richer answer to many problems.

Super appreciate all of your individual suggestions and it has already helped my buy box.

Arman, the mid west is booming in a lot of my research. What are your top markets? And Why?

Amit the drive by test is so powerful. I would want to visit any out of town properties before investing to get a feel for the place. I don’t think I have any experience to back this thought as I do not know what I would look for intuitively yet!

Ken your thoughts are simply true in my eyes.

Take care and happy investing.

Martand Chhibber

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New to Real estate. grateful for any advice and guidance!!!

New to Real estate. grateful for any advice and guidance!!!

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