TP Rollie.
I agree with the part about how Boston is a college town etc too.
Boston is by any metric a great place to live. Despite their grumpiness Bostonians are a pretty decent bunch, lots of money, low crime, and it's a classy town overall. It's a good place for staying out of trouble, and a good place for challenging yourself mentally.
I'm also glad Portland, ME is home to the Red Claws, I couldn't think of a better city for young folks to grow up in. Once you've lived in nice towns like that other cities just don't compare.
Not only are these cities good for their development, but they are nice enough to make players want to stick around come contract time.