As an overall complaint of NH / Boston (I'm also an agent in Boston) right now, the housing stock is just tired, old, and in need of a lot of updating - which is difficult considering pricing and cost of labor, supplies, etc.

@Kusum Chanrai One way to speculate on heavy upside is turning to areas which are soon to be better served by public transportation, for example Chinatown which will soon see the extension of the Muni Metro T Third line through the financial district.

It's like buying a Ferrari when all you need is a bicycle to transport yourself one mile to work.

Try looking at the Metro Housing Boston (formerly MBHP) website.

The city is going through a lot of positive changes not to mention a commuter rail is there taking you to Boston in 20 minutes.

Haven't spent much time in the neighborhood, but there is low crime compared to the rest of Chicago and public transportation nearby. 

I am looking to meet some agents with REI experience that operate south of Boston. 

For public transport, ITP east (Belvedere-ish and out, and west are your best bets, or the south (College Park, East Point, Ft.

If anyone is familiar with massachusetts, the areas vary widely- cape cod, new bedford, taunton, south shore, and of course boston itself (out of my league d/t price) are all much different in price/rent ratio, schools, crime, etc... what are the things that matter most to you and influence your decisions when looking into different markets?

Looking for a Tax Advisor that specializes in Real Estate Investing/Flipping in the Boston or North Shore area