The Chileans built a ripper 3 seater from the trailer they use to haul all thier gear up into the mountains.
relly its an obvious thing to do to maximize the fun. you will need a big sail or lots of mounts for your other yachts mast.
i say go for it!!!!! make sure you post photos

we once hooked a class 5 to the back of a quadbike for filming and it could push the quad quite easily.

The trailer sailor idea is in the back of the mind for a final race at a Pacrim.
Right next to Donnas Lounge chair sailors race