Circuit Guy ... would love to have two communities but I don't dream that big ... it would be nice to have others participating ... being of like mind ... and available for cooperative projects and mutual aid .... but since its so hard to get a cooperative project going let alone picking up lock stock and barrel.... I only envision a personal/family size plan. It would be great to have others but ..... if you wait for others things rarely happen.

I have found a small island in the Caribbean where R E taxes are low ... real low ... residency can be had for buying a property of 100K or more...
The boat is a motor/sailboat ..... big enough to take some cargo....
Nova Scotia is actually warmer in winter and usually a little cooler in summer than Boston Ma.
The land and housing up there is quite reasonablely priced .. taxes on R E not too bad... Can stay as a tourist for up to six months without a problem .

"Caribbean/Nova Scotia and a boat to go between them. "
Are you imagining a two communities that are part support a ship that goes between them in international waters where startups can pull people from all countries w/o immigration issues and operate with less regulatory difficulty? The mundane stuff would happen in the Caribbean and Canadian communities, and the ship would be their innovation center?

BVI/Curacao or NZ/Fiji and a cruising catamaran.

Stay away from the USA.

Cold/Warm--Blizzards & Mosquitos/Hurricanes & Mosquitos... I don't know, the only winner NS has over the Caribbean is that there's no Cuba, and the only winner the Caribb has over NS is that you won't freeze.

My mother lived on a large catamaran based in the Caribbean for many years. It was paradise. I enjoyed the Bahamas. She spent time there, a few remote Mexican islands, Cuba, Belize, etc. I remember after she returned to visit after her first year on the boat. She actually looked 10 years younger. Oh, and the tax man was after her. They don't like letting people with money leave the U.S.