Jim,
This sounds like a great idea. I used to "surf" my Dart 16 down the face of 2-6 ft breaking waves and over a sandbar break on Cape Cod. The Dart was similiar to the wave (no boom, no boards) The guys that would be able to deal with a surf/sail event would be the sailors who surf. The sailors that dont surf probably cant visualize what you are thinking about. Dont let the naysayers get you down on this... go find a bunch of sailers who surf or surf kayk. And make sure everyone wears a helmet if it gets over a couple of feet.