OK, that's a whole conversation by itself, so I moved it to a new topic.
It totally get you (I think). I didn't know how "the system" worked, except that I knew about those expensive (and exclusive) yacht clubs. And my attitudes about clubs being not that far from Groucho Marx, and my willingness to spend money on exclusivity about zero, that kept me on land. I knew of, more than knew, one guy who was plugged into the sailing scene, and could have introduced me to boat owners, but felt uncomfortable about the idea. And, in retrospect, big boats would not have been a good starting point.
After a long time watching from shore, I came across a convenient place to launch a small boat, and bought a tiny rowing dinghy with sail kit; small enough for one person to drag or two people to carry across the beach. Barely big enough to fit, but only one sail, and, we a full-size adult as ballast, surprisingly stable. I spent a couple of years in that boat getting my bearings and sorting our some ideas about sailing. I prefer experimenting over being taught, but that should not come as surprise.
One day, a friend came and said "I've found your boat". Didn't know I really needed another boat just then, but he acted as surveyor and graciously helped out with the maiden voyage and to get me to the rudiments of sailing with a jib. That's when I started with the DS. The funny part is, that I was so used to single handing that small boat, that I didn't hesitate to sail the DS on my own (or with very young crew) almost from the beginning. Not exclusively, mind you, over the years I've had 80 different people on board, from passengers to occasional to steady crew.
Fast forward a number of years, and I get a bit tired of the "lone wolf" routine. So, I check out the local "racing" scene. "Racing" has to be in quotes, because the best event in town isn't a serious race. It's (almost) a free-for all, definitely low on rules and exclusivity and equally definitely focused on the fun of it. I'm told that at the height of the season, they never draw fewer than a hundred boats, from 9' to 70', cat rigged to schooner. No membership necessary, you just show up....
I had known about this for a while, but somehow never "managed" to be out on the water at the right time. So, I grabbed the chance when, one year, they held an opening party. Got to meet the "competition" and a potential crew. Before I knew it, I had sailing friends - a whole group of them. And they own other boats, so now I'm out on the water on big boats too, or crewing on other dinghies. (And the big boats are members of a "yacht" club: on paper, no clubhouse, no exclusivity).
Fast forward a few more years, and I'm about to push off the dock when someone (I can't see them through the mainsail that stubbornly refuses to hoist) tells me: "your reef line is fouled". There's someone just sitting there, with the full appearance of someone whose ride hasn't shown up. But clearly knowledgeable about sailboats. So, we take a chance and add her as a third wheel to the crew for that evening's race. Means our fight for last place becomes that much easier

, but we've never had as much fun, and so the circle closes.
I think that's how sailing is going to be built - by people seeking connection, looking for shared time on the water, exchanging experience, inviting others in, until someone comes along who sticks around. And small boats, like the DS are definitely in the center of this, because of their low overhead and their flexibility. Sure, a Laser is smaller, but where do you put your crew, or the passengers?
As for hooking up with people of like interest, the modern tools give you all the convenience. The last person I invited on board came via facebook. Any place that has a bit of a sailing scene has one or two preferred (or simply successful) online methods the locals use to find boats or crew. Or, you could auction off a dozen "afternoons on the water" at your school, church, or wherever people do auctions. Give a limited range of dates and encourage the lucky bidder to pass on the voucher if they can't make it themselves. One way or the other, you're going to come across someone who's been looking for this and will stick with it on a regular basis.
I know people who have sailed a dinghy in the local "race" for over 20 years - I think the fact that there's a regular schedule has more to do with the success of this than the competition. It's much easier to meet regularly than having to figure out whether it will happen or not. The same is true for yearly or monthly events. Perhaps you are part of a group that will start something like a regular cruise or daysail. In that case, best of luck.