Here's a few quick thoughts after a few years working similar issues with this club South Winds Sailing Club, Lake Allatoona, Atlanta Georgia, Sailboat Racing, Cruising, Family Fun, Sailing Atlanta -Hi everybody,
I was press ganged into being the VC Sailing for next season. We are a very small community based club of about forty members.
We currently only have one sailing event in August, and I'd like to expand it considerably. The age of the membership is decidely in the 50 plus demographic, but there have been some younger members joining.
Lot's of conundrums in the challenge you face.... LOT'S .........
Try to get 'buy in' from at least half the members as to ' what they want' - fun club racing/fun sailing events or 'standard racing' ... probably start with fun events and morph if the attendance/interest warrants.
Members grow weary of seeing same boats/skippers winning all the races/getting all the trophies - but many won't make the effort to improve.
The slower boats enjoy being out in front so consider 'pursuit race' formats with the faster boats starting last and chasing the slower boats.
Skippers new to racing are often reluctant to 'mix it up' with experienced skippers - invite newbies to crew to get some exposure and encourage them to 'sail along on the fringe' of the fleet on a casual race to avoid the close quarter maneuvering.
Poker runs, club 'cruises', a 'Chili dash' can all help to get members out on the water sailing in close company with other boats .... if there's two boats nearby, there's a race going on in at least one cockpit
Handicapping is the necessary evil of club racing - good luck with this one when the goal is trying to spread the trophies around in an 'equitable manner'...
Every skipper has an opinion of what works, what's best, etc - too long a topic for this post but I go back to 'get buy in' from the members - I will say that I'm of the opinion that for casual, fun, local club racing - a modified system (PHRF or Portsmouth based) that adjusts/squeezes the fleet by seasonally adjusting individual handicaps provides the opportunity to keep corrected times close enough that folks feel like they have a chance to win ... and that equals fun ........ conundrums abound !!!
Good luck (PM me if you'd like a detailed discussion)