I can see your choice for Blue Hill for your work commute. "Overqualified" is a common theme on not finding work around here I'm afraid.
Some people thrive in the more remote side of life here on the coast, and others don't as much. I've lived quite a bit of my life in a beautiful rural area. It was great for a lot of things but we were looking for some other things this time and feel pretty lucky here. Most everything we like is close by so we drive very little. When we do drive it is to get to more urban areas like Portland, Boston and NYC for numerous reasons. We realize then we're a bit remote here.
Something I've run into more than once are people moving into the more suburban neighborhoods on the outskirts in this area of the coast.
Most have retired at least partially, and soon find, they're driving into the village centers, for coffee shops, art, classes, walking, the harbors, to sail, to go to restaurants, the librarys, the shows, you name it.
Everything they came to retire to, they didn't think about getting to it when they bought their house. So a sort of hopscotch goes on. That's good for realators I guess.
I'm with you on sailing in your new grounds. We love to get down that way, it's beautiful, and the sailing is fantastic. I can see why you choose to live there.