Re: race participation
Often what intimidates reluctant 'racers' is the worry of flying a spinnaker, or the worry of not having a spinnaker (or knowing/wanting to use one) etc.. For that group a 'non flying sails' division keeps things simple, and you'll often get more professed cruisers willing to take part. Providing them a separate start (the other major intimidating feature of 'racing') helps too. The Pursuit style makes things a lot more fun for the slow boats, as mentioned already.
We've also, in the past, put 'better' sailors on other boats to speed them up and get them a taste of being in the thick of it. Lots of learning to go around, and finally a casual debriefing at the end of the day, a few suds and discussions about what he/she shoulda coulda done in that situation is always a lot of fun, adds to the social dimension and makes for closer friendships among the 'competitors'..
".. there is much you could do at sea with common sense.. and very little you could do without it.."
Capt G E Ericson (from "The Cruel Sea" by Nicholas Monsarrat)
1984 Fast/Nicholson 345 "FastForward"