I have heard complaints about portsmouth and frankenboats in the local clubs in my area as well. I've been tossing an idea around in my head but I have never mentioned it before now...

What if the skipper was rated instead of the boat? It would be a portsmouth style system where a skipper's (rather than the boat's) rating would adjust after every regatta. With such a system, you would win races more based on how much you (or your boat) has improved.

In the particular case being discussed here, the skipper's (Dave's?) rating would progressively decrease every time he won the regatta. In order to keep winning, he would need to either improve his boat each year, or become a better sailor.

Gaming such a system would require the skipper to intentionally loose regattas to keep his rating high. Somehow I don't think that would be much of a problem!