Their job is to maximize your investment, not cost you money.

They aren't going to say, "well, the neighborhood is going to crap and I'm tired of the vacancies"...instead, "long time owner wants to retire", "need more space", "job transfer", etc.Get a conversation going first on price (via an offer), then work in these inquiries.

I am not fearful when I do my job but I do use professionals where professional skills are called for.

Part of your job as a realtor is to bring listings into the brokerage.

Why is this a complete gut job? 

I really want to quit my day job.

This is because it's a 40 minute drive, and I do not have time to screen and meet for showings, with my full time job.

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.