Yes Tom a lot of what you say sounds familiar. We moved to Maine in 1993 as I accepted a faculty position at UMaine Orono. We looked for property mid-coast where you are Camden/Rockport area and it was very nice but just too far from Orono, so we settled on the Blue Hill peninsula. My wife was elementary ed and masters + 30 or so and couldn't get hired anywhere - overqualified. As you say, tough to find any kind of employment. We were doing ok and had a home on the water with a dock for the boat, but what eventually drove us out was just what you said, the seasonal desolation come the end of October. On a weekend night in the winter there wasn't a restaurant in commuting distance. Bar Harbor had nothing, Ellsworth ditto, Castine, even Bangor had very little to choose from and too far anyway. Man, it was desolate. And as you said, the first time I filed a tax return the state tax took my breath away . I can't see where people retire in Maine; high income tax, high cost of living, questionable health care for elderly, difficult to get around in the winter. Anyway, I'm back in southern RI where I grew up and sail out of Point Judith. Been to Maine 5 times since 2000 but I think we may not return any time soon after the lobster pot challenges of the last few trips. After 18 cruises from Kennebunkport to Grand Manaan, we've kinda seen a lot of the coast. Gonna work on Long Island for awhile. Maine is beautiful and unique cruising ground tho.