What town do you live in in MA where the families are multi-generational? I grew up in MA in a large town with a HUGE immigrant population; I don’t think I knew a single kid growing up who had roots in MA let alone in the US. And the state has become MORE diverse since I left, not less.]
I think kicking the tires on a couple of the Mass state schools will be a good exercise to get your son to realize that the state IS extremely diverse, no, it’s not the South but there are kids from ALL OVER. He will find his peeps in college. I hated HS but loved college, and I know dozens of adults who had the same experience. A big college is going to have lots and lots of different kinds of people and he will be less of a fish out of water than he’s been in HS, especially if you’re in a small, clubby town.
Are you sure that even with merit aid the schools on his list are affordable? In addition to tuition, room, board, and health insurance, you’re going to need to fly him home from those distances and that starts to add up… do you have an affordable option besides U Maine? (assuming that comes in under budget?)