Hi Michael, Kathy,
Boston based and just invested in Pittsfield for a couple of reasons, including the overall direction of the city.
Here is my take for what its worth:
City is being well managed with an active strategic plan involving the arts and the "hipster environment" and there are a few encouraging trends within the overall picture specific to Pittsfield. Hospital is a strong draw, and there is a burgeoning migration to these types of cities. Milennial/Gen X families and young adults (the demo that spikes outward migration) are leaving the Bostons and NYCs in search of lower housing costs, but they want the restaurants and culture. Pittsfield is well situated via rail to Boston as well as NYC (and Albany).
Pittsfields doing really well with Art and Culture/restaurants and its a key piece of the strategic plan, new minor league summer team run by the Bill Veeck group, lots of music and the downtown district appealing. New Hotel on North is a chic boutique hotel which was a 15M investment by an experienced Berkshire family. Big emphasis on redoing the cityscape and making the downtown feel safer to people. It is safe, but compared to the rest of the area doesn't look that way and has a bad reputation from long ago
GE's legacy is complicated and they left Pittsfield high and dry in the 80s, but to a large extent the city has already taken its hit (lost something like 40% of it jobs in the 80s). Lots of affection for it and some glimmers of people moving back. General Dynamics is joining in the push to attract the young 20 30 something population because it needs the talent. Hospital now largest employer and I think the downtown is becoming a haven for the restaurant and service industry types who are priced out of the Lenoxes etc but still work there. Organic coffee shops opening, etc. Needs small retail and more traffic.
Don't mean to sound like the chamber of commerce but I do think the town is poised to be a great micro-market.
I'd be glad to talk PM if you are interested.
Best,
Jon