We are a commune of inquiring, skeptical, politically centrist, capitalist, anglophile, traditionalist New England Yankee humans, humanoids, and animals with many interests beyond and above politics. Each of us has had a high-school education (or GED), but all had ADD so didn't pay attention very well, especially the dogs. Each one of us does "try my best to be just like I am," and none of us enjoys working for others, including for Maggie, from whom we receive neither a nickel nor a dime. Freedom from nags, cranks, government, do-gooders, control-freaks and idiots is all that we ask for.
Cuttyhunk seems remote, but it is only ten minutes by air from New Bedford. I don't know how well Amazon Prime works there. Cell service? Don't count on it. Around 40 people live on Cuttyhunk year-round.
Cuttyhunk is a lovely place, but certainly remote. I'm not aware of there being an airfield there, the terrain is hilly so you better fly in by helicopter.
My visits have all been by sailboat, never in winter. You would have to transport fuel (wood) by boat, the main channel and harbor will not accommodate a large vessel. Might be best to close up the place in the cold months, spend the winter on the mainland - might even be cheaper than transporting the volume of wood you would need to heat the place.
It's a great place to visit. There's a ferry a couple times a day in-season from New Bedford, by the city dock. Lots of places to rent. A couple part time restaurants. There is "nothing to do" so everybody fishes, drinks, plays cards, swims, horseshoes, whatever. Good fishing charters, wholesome activities for younger kids. Dry island, only one shop, so you have to bring whatever food and booze you'll need during your stay. It's sort of the opposite of Hyannisport or Marthas, a little like Wellfleet but even moreso.