Feeling overwhelmed... how do I choose an area or location to invest?

[Steve Candor]

I travel every once and a while through Connecticut and Massachusetts. So I'm looking to purchase a multifamily in one of these two states. Prefer Western MA to anywhere along I-91 or I-95 in Connecticut.

Looking for something in the under 250k range - prefer 150k that I can pay all cash and return good cash-flow positive. I do not care about appreciation as much as positive cash flow. 

How do I find a good area or location to invest? I don't mind a fixer upper.