Jake,
I don't expect what I'm about to propose will ever come about but what the heck it's a lot of fun.

In fact some of the most fun I've every had sailing is when we do boat handicappng.

We run a short race and from that race we developed a handicap.
Now instead of the handicap staying with the skipper it was given to the boat. So now you have the relative speed the owner(someone who knows the boat intimately) can get it around the race course.

Then everyone swaps boats and they have to outsail the handicap developed by the owners race.

When we sawap again for the next race and still you are sailing with the handicap the owner established.

At the end of the day (after 7 races) the best sailor, not the best boat wins.

It is an awful lot of fun when we do it as we all enjoy the clowning around between races as well as during them.
It's not for everyone some people still think we're sailing for sheep stations.

Just for fun.

Phill