About To Do It Questions
The "pirate" knows (and writes colorfully...) of what he speaks. There are challenges to wintering over in the North. Consult marinas where they prepare boats for this...plastic covers over sturdy (make that complex and $$$) framework, boat prep against freezing (can lead to sinking), constant battles against humidity and location challenges; snow removal, parking lot access, storm protection .. well you get the idea.
I''ve seen winter "livaboards" in Toronto and also in Maine. It doesn''t seem practical for someone who travels a lot.
Anything can be done for $$$$$.
As for the pirates advice? I disagree about the condo in NJ ... wrong state, sir. Like the boat, the condo would have to be much further south of the frostline to suit me.
Fair winds to you all.