As I was reading this post I was wondering, is there some sort of reversed handicap used by anyone? By this I mean that the extra time added to each sailor because of handicap is given at the beginning of the race, and not the end.
Say theres a regatta thats X distance long, between an H16, a Tornado, and a Blade F16. The distance is caulculated before the race and instead of everyone starting at the same time, the H16 starts first. Then the Blade f16 start as soon as its horn is sounded when Y time has passed, then the Tornado after Z time has passed. That way you could have a first-to-finish race between these 3 said boats.
Im not very experieced here, sailed alot on a laser so didnt have the problems described here, but I think this might work to some extent. The main problem would be the hassle of finding all the numbers before the race, and you loose the pre-race battles between boats which I find to be very important.