Some areas that come to mind are Plymouth, Falmouth, and Yarmouth.My next steps:-Start networking and build a team who has experience in both rental property investing overall, and the specifics of the Massachusetts region. 

Single family in MA.

I was wondering if anyone is aware of any lobbying groups or organizations in Massachusetts that advocate for LANDLORD rights.

Under Massachusetts law, it is illegal to discriminate against someone because the presence of children might trigger a property owner's duties under the lead paint laws or because someone receives a housing subsidy, such as a Section 8 voucher, to pay for some or all of their rent.

@Jason Ma as a Flipper Brandon's numbers aren't for rehabs but for low end rentals. 

Hey BP,Family has a commercial space currently rented by a mechanic in Dedham Massachusetts that will be vacant Jan 1. - Looking to connect and discuss with a local commercial agent about filling the space with a new tenant

Hello, I am looking to rent a single family in MA. 

That being said, many of the courses from the MA in RE degree you outlined are offered online and in person in NY.

My dad is an accountant and real estate investor in a college town in Western Massachusetts, so I guess that rubbed off on me.

So, my wife and I house hacked a 2 family a few years ago in Massachusetts.