Re: race participation
From personal experience some thoughts toward a laid back approach focused on getting the other 80 boats to the starting line:
1. Make it easy for people to show up. Offer to rate their boat and be generous.
2. be very liberal on sail numbers and placement.
3. Relaxed rules... anyone who lodges a protest has to buy a round (or 3) for the opponent.
4. No one likes coming in last. Consider reverse starts where the start is staggered by PHRF rating. Slowest boat starts first and the fastest goes last. Makes for an interesting finish.
5. If someone comes in last often enough, they'll stop showing up. Offer a post race review of any individual boat's performance. Make it a round table where more experienced racers can tell the slower boats what they did wrong.
6. Discourage sport boats or exotic sails (Code 0, etc.). Encourage pummeling with water balloons anyone with laminate sails.
7. Party doesn't start until the last boat is tied up.
Sabre 38 "Victoria"