I disagree. In this economy I've seen perfectly good 30 foot boats go for peanuts. Last spring my storage yard let a 32 foot Islander in nice condition with a 1 year old diesel go for $4K (in CT), basically back storage charges owed to the yard. It is plenty big enough to live on in a warm climate, althought the draft was a bit much on that one. There are plenty of people out there willing to dump a boat just to get rid of it right now. I think you should be able to find a decent something for $10K and then use the extra money for a few extras. Very doable on $20K.