Amherst native here, just got back from spending Christmas in the area. I agree that it’s got a hell of a lot going for it for a relatively small town, but would argue that nearby Northampton has a better and more walkable downtown core. I have a midsized gang of childhood friends who either stayed in or returned to the area, and nearly all of them drive all the time; those who don’t are mostly hardcore bicyclists.
Desirable housing can also be expensive relative to local incomes—people I know who have bought homes in the area recently have ended up in Hadley (mostly not at all walkable) and Easthampton (only a few central walkable square blocks), or farther out into the (decidedly non-walkable) hilltowns, rather than being comfortably able to afford either Amherst or Noho. Perhaps rents for the new construction apartments in downtown Amherst aren’t bad, though; I dunno.>>2382821
I had a good time in Madison, Wisconsin, when I went to grad school there. The central isthmus is dense and walkable, and less-central neighborhoods are mostly bikeable. And it wasn’t terribly expensive when I lived there (cheaper than MA), but I assume there are many more expensive new condo/apartment developments downtown that could have driven COL/rents up. So depending on where you are now it might or might not be affordable. But it’s not big-city expensive despite almost feeling like a city.