I always look at used sail boats and every so often (well, pretty often) I find something that looks like a real deal. Most recently there was a 27 footer something-or-other in great shape for $3500, and it was just a few miles away on the same lake. Due to my current situation buying anything is out of the question right now (more political than economic, but that's another story) but it got me to thinking about cost of ownership of a sailboat. I paid $1200 for my 22, slightly below market, it was ready to sail but basic, came with a trailer and motor and 2 good (enough) sails. I've since made some improvements to the tune of about $6000 total cost, and that does not include slip fees or insurance. No way I could sell it for anywhere near that price, probably the best I could get is $2000 and that would be on a good day. So the same market that shows me attractive deals is also responsible for instant depreciation to $0 of any money I dump into the (any) boat. My optimistic view of this situation is that I could be throwing money away on a bigger boat and be getting the same return for my investment. So I've declared my boat 'finished' (as in stop the bleeding), and when my daughter finishes college in a few years (please hurry) I'll go hunting for the next big thing.