But the family part sounds tough. Change is hard, especially for some as they get older. But change is happening at JO Brown's anyway, it's a slow disintegration of their facilities!
Then there is the small Maine harbor village. Unless most are behind the idea, people can make it tough for you. Quite a wide range of inhabitants on NH today.
Maine boatyards/marinas have a short season on the docks so they have to be year round businesses to survive. I think they would draw boats to their docks and facilities(and work year round to sheds with roofs...).
The Fox Island Thoroughfare is a busy stretch of water with transient boats headed downeast and west. General facilities and provisions-etc, would fill the docks during season. Don't hold your breath,....