Racers want to fill their crews with the most experienced, skilled people they can find. If you have those skills, you're likely to get invited aboard. The last people chosen will be the ones with the least experience. If you don't have experience, then your best likelihood to get on board a racing yacht is to go to the docks from which racers are leaving on race day, and ask them if anyone needs extra crew. Often they don't need skilled crew. They just need extra crew on the rail. Go out with them, and watch, and listen, and learn. After you have developed some skills, you'll be invited back. The hard truth is that you have to learn and earn a position on a race boat. Don't think you're the only person with this problem. I have often had to prove myself, even though I've had a good racing record for 30 years. The skipper of a racing boat has no way of knowing how good you are until you show him. Don't be discouraged. It takes time.
Yeah, I imagine there are one or two fleets on the Chesapeake where skippers can be that picky, but even then its probably bad for racing overall.
At most other places, skippers are willing to take folks on and give some OJT in order to build a base of crew they can call on. I know I never would have been aboard a sailboat in a race were it not for Fishing Bay Yacht Clubs crew recuiting efforts. The boat I ended up crewing on had a few life time sailors, a couple of evolving landlubbers, and my wife and with experince levels between those extremes. They were thrilled to death when after the first tack on our first time aboard my wife coiled the lazy sheet and prepared it for the next tack and we've been invited back ever since. I've done a bunch or around the bouys races, a few long distance races and did Down the Bay from Annapolis to Hampton with these guys. In all that time we often would have a new guy aboard so the skipper has a cadre to call on. FBYC actively recruits and trains landlubbers to provide crew for their skippers. They do both land based training before the season starts and on the water training before the spring series starts so even a greenhorn will come aboard with a clue as to what's going on.
The experience I got through participting with FBYC gave me the confidence to enter my own boat in a couple of races, and I might try some more. I don't think I'd ever raced my boat, without having had the opportunty to crew, so I can attest to any club official reading this that outreach programs are important if you are trying to build a fleet/promote sailboat racing.
The fact is that there are only a few fleets where its so competitive that a boat can't afford some developmental crew, and developing crew is important for racing overall and the future of the sailing club. Clubs should recognize this and promote crew development in their "beer can" fleets. Where else are the experienced crew for the hot fleets going to come from?