This whole proximity to Boston thing is a bit strange to me. If that's really what he wants, then he might as well play in Boston and Boston only.
Playing in say, the NYC metro area, which is the nearest location to Boston of all the teams he is considering (other than Boston)... it would still be a 4.5 hour drive. It's not like it's just a hop, skip, and a jump away.
It's a 1 hour flight, sure, but then Chicago to Boston is only around 2 hours.
So basically.... if what he REALLY wants is to be close to Boston, then he might as well play in Boston.
And if that is what ends up happening, then I don't get why he even bothered to meet with all the other teams, unless he just liked to be wined and dined even though he knew he really had no intention of signing with them.