I sold my house this year and am living on my boat until I decide if I like it enough to buy a larger boat or go back and buy another house and keep this boat.
I understand ATM''s are becoming very widespread and since they often have the best exchange rates, I would carry as little cash as I was comfortable having.
I would think if you are in reasonable shape that you would not have any problem handling a boat of 36 to 40 feet as long as you prepare and are conservative. On my boat there is a huge increase in effort needed to bring the in the second reef when the wind is gusting to 40mph over doing it at 25mph and laughing when the gusts come.
I ran into a friend I hadn''t seen in 10 years or so and he suprised me in mentioning that although he no longer teaches SCUBA, he still has to carry insurance, since people he taught are out there diving. I don''t know if dive masters have the same liability when they aren''t working. If you are diving I can''t recommend DAN insurance enough, especially if you are in the Carribean because a flight to a chamber equipped hospital could run into many thousands of dollars, not to mention time in the chamber.