OK, thanks for a very prompt reply I'll take the questions in the same order.
Boat: Currently Hunter 41DS. Seriously considering Beneteau Sense 50.
Reasonably experienced sailors altho my wife is very reluctant to do night watches on her own.
Have not "lived" aboard. Max time at any one time 2 weeks.
Know nothing about the area, just need to be nearer the US and family all of whom live there.
I know it's a dream but unless you give it a go, you'll never know and I don't want to go to my grave saying "...if only"