I've seen the F18 guys trailer their boat backwards on the trailer and I'm wondering if anyone with a 16 has done it.

To me, it seems like it would solve all the problems of having step-ladders and tripods when solo-raising the mast. Just slide the mast towards the front of the trailer (while still on the mast support) and pin it. One might have to use a few pulleys if they want to use a winch at the front of the trailer.

Is there a reason why this wouldn't work?