Two quick moves: pick a simple buy box now (duplex/triplex, target towns outside Boston, rent range) and practice underwriting a few real listings each week, then ask a local PM to sanity‑check your rents and expenses.Which MA submarkets are you leaning toward, and what’s your initial buy box so we can tighten it? 

Hi @Ryan Tobin from my understanding In Boston, a lodging house license is generally required if you rent to four or more unrelated people.

I totally get the challenge of getting started in a high-priced market like Greater Boston, especially with down payments for multi-family properties.

Single family with an in law might be a good bet for house hacking, btw.Quincy has some definite upside and i think is still an “inefficient market” growing around public transportation. and i would check out hyde park in boston for growing gentrification as well as neponset ave and morrisey  blvd in dorchester where a ton of development is planned 

Boston remains a top multifamily market, driven by its world-class educational institutions like MIT and Harvard.

Gains are concentrated in healthcare and food services, while sectors like transportation, warehousing, and manufacturing are shedding jobs.

Recommend as before you look up State Transportation department land sales.  

Across our meetups in Worcester, Lowell, Waltham, Portsmouth, Manchester, Biddeford, Northboro, Boston, Lewiston, Hartford, and Medford, this question comes up constantly this time of year.

This morning he texted me saying he has a new opportunity in Boston and asking if I'd be open to him subleasing it.

In in Greater Boston atleast once a week.