I studied a lotta maps around Connecticut, Rhode Island, Massachusetts, New Hampshire, & Maine before I picked that spot.
Maine was too far North for the mild Winter depicted in the game....New Hampshire has very little coastline....Massachusetts too crowded....Connecticut has all it's coastline to the South....So I finally settled on a spot in Rhode Island, around coordinates 41.60000, -71.41888. Wasn't perfect, but it would do. In actuality, there is a Golf Course and Airport there.
Shame they couldn't have made it a little more obvious, like some of the GTA locations.
What would have been far better is to have had an actual coastline....Or make the spot where the School was located like a tiny island, with the sea to the South.