Steve, here's a great story
about another guy. He was a little older than you when he decided to pursue his dream.
As for finding work around the docks? My suggestion is to avoid the yacht club proper, and hang around other folk who are cleaning/fixing boats, etcetera. Offer to help out. Get to know them and let them know you. Then, next time they might need help being hosted in a bosun chair, or installing deck hardware, they might ask you. Also, check at your local chandlery to see if they're hiring. Since, at this point in time, sailing seems to be your passion.
Being able to get sponsored for racing seems to be the ticket. Though, I respectfully disagree with George, who seems to think you have to have a lifetime of sailing under your belt and be a who's who to get sponsorships. Imho, Ronnie is proof that is not the case. Though, he did find a niche, and that is giving back to fellow wounded veterans. Which arguably helps to lure sponsors. Still, he had to be able to sail and he had to be good enough to get their attention.
Don't know how you're funding your boat... hopefully with the guy who sold it to you as opposed to a bank. If so, he is likely to be much more forgiving than a bank... as long as you are able to send regular payments. If you have it paid off, then, that's even better.
As for shoulda, coulda, wouldas? What I have always told my kids, follow your passion. Shoot, I'm an old fart, and still following my passion. Even if that means learning to sail a dinky dink!
Anyway, just some off-the-top-of-my-head thoughts. Please feel free to take what you want and heave the rest. ^_~