Great responses... thanks... maybe I should've given a little bit more info...
We race Flying Scots and Sunfish as 1 designs... most FS days have 3 races, most SF days have 5... we used to get 3-4 days for each class in each of 3 series, Spring, Summer, and Fall. Frostbiting the fish was handled separately and wasn't club sanctioned. Trophies for 1st 2nd and 3rd in each series, great participation. For a long time, the obvious season champ in each class was the same guy who shall remain nameless, but he just couldn't be beat. Once he retired from racing, a season champ was named in each class.
There was always one race per year for All Boats which would draw participation from cruisers. Over the years our 1-design fleet has been dwindling, at the same time the All Boat races have been expanded and participation has grown. But often the Scot's races in these standalone races, and we still need to name a season FS champ... Contrasting with what WYC is doing, our attitude is that after the intense lockdown the NY went into, the closer we can get to normalcy in the shortest timeframe without taking undo risk, the better all of our chances are of keeping our sanity.
David touched on something that has allowed me to be successful over the past couple years... maybe this one too... a good friend of mine sails an S2 7.9 ... absolutely blows away the rest of us... but he gets bored and sometimes races in his C-Scow instead, or on his windsurfer, or on a mutual friends Capri 18, etc... while each race gets its own trophy, the season champ in the not-1-design division is called the Champion Cruising Boat ... so the apparent logic from the race committee over the past few years has been that when he races in a boat that isn't a cruiser, he scores a DNC in the scoring for Champion Cruising Boat... it's only this year that I convinced the comittee to create a Centerboard class so his scow races handicapped against the Scots...
So ultimately, only one response so far for optoin #1, which is the way I would lean, and no responses for 2 or 3...