Maltese Falcon
It's big, really, really big. It's nice, really, really nice. But it sort of sucks too. It can't be taken too many places, it takes a huge crew to sail (meaning that even the owner isn't going to be in charge on trips, it'll be a Captain who can actually sail the thing), and it's just too over the top.
I would sort of like to see it sink, or be scuttled, since he's really only into the design process anyway - sinking it on purpose would be really cool and a great statement!
Or he could sell it on eBay, that'd be cool too.