Re: Singlehanding a 41' Hunter DS?
One thing to think about. Been to Florida, but never lived there, but in the summer, I hear air conditioning is pretty much mandatory. It probaby is not the most fun thing to be cooped up in a sail boat with ac going. A catamaran or power boat with its sliding door and more room would probably work better.
I am with you on moving out of NY. I lived in the north east all my life and getting to a year round warm climate was a great change- one you could probably use. Florida sounds like a great place. I would look into joining a sailing club, and just chartering some big boats for now.