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One group I know of has what they call the "Po'boy Handicap Racing Fleet" which is done similarly to what has been described. The fastest/best boat is the rabbit boat, ergo all ratings shift round him. Effectively the skipper, not the boat, is rated. They also do staggered starts.
Trophies are booze, with the end-of-season/series a nice perpetual.

But it doesn't have to just be racing....
Overnight rendezvous? Sail out, camp somewhere, sail back.
Raft-ups.
Travel in a group to somewhere that takes a couple days.
Poker run.
Moonlight sails.
Have it as a goal to bring new people out.
 

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In my case:

The boats are assigned ratings. The slowest-rated boat starts first, and everyone else is staggered-start afterward, according to their ratings.

We don't have a line. Someone will set a mark in a prearranged spot, which is always the same, it's listed on the SI. All you gotta do to start is be somewhere fairly near the mark at the assigned start time. Last boat to finish has to pick up the mark and bring it back.

The 'rabbit' boat may be the fastest rated, or not, but the 'rabbit' is the only boat whose rating does not change throughout the season. Everyone who beats him gets adjusted to a faster rating, everyone who is behind him gets adjusted to a slower rating. Changes depend on how far in front or behind they finish.

There is also the factor of race-course. In our case, we generally do not adjust ratings if we can't get a course that has a reach, a run, and a beat, all three. This makes it fair to all boat types.

Your 'rabbit' has to be onboard with the concept and pretty much ok with rarely winning. In my example the 'rabbit' is the most experienced, dedicated racer in the bunch. In fact, it was he who has been developing our club's rating system in order to encourage the 'cruising' sailors to come out and play. The trick is to make sure that everyone understands that the ratings will not apply anywhere else, but the thing is, most of our guys wouldn't bother to race at all except for our system.

--oh, btw, we don't use spinnakers, although people are allowed to pole jibs out.
 

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--oh, I forgot until paulk reminded me, funny trophies:

The Po'boys have a last-place seasonal award, the "Lame Duck," which is a fairly large rubber-duckie wearing a little sailor hat. The winners (losers?) get a dog-tag engraved with their names, and the tags are hung round the rubber-duckie's neck. Keeper trophy is a tub-size rubber duckie.

The Best Breasts award at what is a sort of serious race, the Juana Good Time Regatta, which is a couple of toilet plungers mounted to a piece of wood
 
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