It's entirely possible that he'd get started in MA politics at the same time as one of the Bush boys.
And I could see the Bush family going out of their way to curb stomp him. For all of the genteel persona they looked to present they could be quite nasty when they saw fit and I don't think they would appreciate a challenge from the son of another Republican scion. IMO they would do their best to send Mitt packing to Michigan or even Utah.