I was not thinking in terms of professional racing circuits. I was thinking in terms of the kinds of regular, round-the-cans regattas that all us "normal" sailors go to. What if some of those were able to get sponsorship that provided prize money in addition to trophies?

NOT money that would come out of the pockets of the sailors themselves -- entry fees would be the same as usual. Everything would be the same as usual, EXCEPT for the money prizes.