Trailers cost too fricking much too. I bought a new enclosed trailer for work almost two years ago. $15k, it's a little guy at 7x18. I would've got a 16' like my old trailer, but wanted to be able to knock the boat apart and throw it in there for major regattas.

When I win the lottery I'm doing a 40' fifth wheel behind a two ton with 20' of toy hauler in the back and quarters in front. The trick would be to do ramp doors in the sides that you could strap the boat to, then just flip it up and close it. You'd still have room for a motorcycle, a 2nd boat (with another door), and probably a Rhino.