I understand that it would be a serious undertaking with rezoning, permitting, etc, so I'm in need of some assistance from an investor/contractor familiar with the process in Boston.I would love to hook up with a contractor that's willing to take on the job and work through the process with me. 

Do have a FT job, 401K etc and are comfortable, and just want some extra money on the side?

Scenario: I own a 2 bd/1bath small condo in SE Michigan (Ann Arbor/Ypsilanti area @ ~850 sq ft) which I lived in for ~ 15 years (nice small place along quiet, decent-sized lake), and moved recently out of state for a different job in same industry.

I'm currently working under a general contractor by day, a job I took with the intention of getting into fix & flip, which will be my main strategy for the first while.

Though I think I will switch to a less paying, more flexible job when I match my current salary.

I found this great list by Forbes which is based on property prices and jobs growth.

When tax season comes, we give our CPA access to our QB and send him our W9s from our personal jobs as well.He handles the taxes for the LLC as well as us personally. 

If I were investing out of my market I would be a lot more sophisticated in my research. mainly I would be watching job growth.

Don't forget this is the person who will performing your due diligence for your tenant screening, and part of his job is to sign those tenants to leases (contracts.) 

Partnership Title Co - Denise Minton does an excellent job and handles all my personal investment closings and most of the closings for my clients.