Are you going to be looking for schools to teach underprivileged communities or more high end boarding schools in elite communities? I think that will make a big difference where you should start.

Look up the mbta commuter rails and see if any of the schools you’re interested in fall on or near those. They are reliable and cheap and can save you the pain of car commuting.

Also the red line goes south from Boston to Quincy/Braintree, so f you want access to the city it’s nice also to live along the red line so you can take the T into downtown Boston whenever you want to go out drinking or do something.