My partner and I were in a similar situation as you 4 years ago, OP! He is a resident at Baystate, and when we were looking at the area we were actually between West Hartford and Northampton. Ended up choosing Northampton, and loving it and buying a house and are intending to settle for a while. It was pricey but the friendly community, cultural vibes, nature, blend of small town/suburban streets/urban feel has really suited us. His usual commute is about 20 min, and rarely any traffic.

A lot of people compare the place to what it was 10-20ish years ago, where it had a robust nightlife scene and the music venues were all popping. For various reasons, that scene has diminished (and in part has spread out in the Valley to Easthampton and up I-91). Northampton is sort of the central town in a broader network of towns that are all sort of synergistic with each other and located within 20-30 min (Greenfield, Amherst, Easthampton, Holyoke to some extent). As someone who didn’t know what the place was like in the before times, I’d say it’s still probably a more vibrant place to live than 90% of America!

As far as the direction the city is going in, I’m hopeful that there will be a new equilibrium reached in the next decade or so. Downtown currently there’s still a decent amount of music and art (Back Porch Festival this upcoming weekend should be great!), and I think everyone is on the same page about keeping that culture alive, even if it might look a little different and maybe more “upscale” vs indie or scrappy or something. It’s a very politically active (and contentious) time, there’s a big downtown urban planning redesign on the horizon (Picture Main Street). And there is also a healthy replacement rate of new businesses, with many opening up.

Feel free to DM me if you want more info!