I agree, offshore roundwinders would be a natural and should be run. Still, for a first shot having the shore nearby might not be a bad idea. You would ease the need for support boats. If guys get tired, particularly if they discover they are on the wrong board for the job they just go to shore. Guys aren't used to having to beat upwind for considerable distances. Not sure why but there it is.
Some old posts about roundwinders appear at:
http://fksa.org/showthread.php?t=657
http://fksa.org/showthread.php?t=724
For most of my roundwinders I have been on some of my longer boards, both directionals and twin tips. The extra edge and fins can serve you well going upwind. As you indicated, if you aren't set up for it, the experience can suck. Yes, would like to try your board. Understand Garry has performed major surgery to repair his board in time for Jupiter.