While this does seem unusual it doesn't seem to be as bad as some are suggesting. If you were to hire a contractor for a $40,000 remodel of a basement, for instance. You would have to pay him a good chunk up front and then installments that were basically prospective payments for his work
. if he ran off you could sue but the chance of getting anything back might not be great if he went bankrupt or skipped town.
In this instance, if you had a $20,000 boat
that was probably selling poorly now and the broker
was going to get a chunk anyway and you agreed to let this guy live on it and sail it while he finished your remodel and then transfer the title at the end of the job it would seem like a standard barter arrangement that used to be quite popular where I was originally from (south/midwest). If he skipped out you report the boat stolen and catch the guy somewhere and get your boat back (or the insurance). If he didn't you get $40,000 worth of work
that you will probably estimate for taxes
to your benefit.
and he gets a boat without having to do all the crap that comes from running a business.
Barter always works out better between people who know each other but I am sure the OP would have references
you could check before doing anything.
I don't have any need nor a cheap
boat but I wouldn't be any more afraid of this situation then many others I have gotten into with supposedly legitimate businesses. (Like my recent boatyard experience that was "only" 30% more then the highest estimate. I should have read that fine print better.