Here's a typical kid (at the helm) on a shared boat from a local Boat Club. While his parents aren't sailors (but member of the boat club), he grew up sailing in local sailing classes typical of any coastal area. Once in college, he taught summer sailing classes here.
There are thousands of these kids (I'm sure), around our coasts with similar backgrounds.
He sailed into this mooring as if he owned this boat even though I think it was the first time he sailed it. The sheet is in the water but I blame that on his Dad (a friend).
About the boat: Most any New England sailor would recognize this is a Cape Dory Typhoon. 19' long, this little boat bucks the trend of many older boats.
A 50+ year old design, nearly 2,000 were built, and I've yet to see one that isn't sought after and worth something, no matter how neglected. In fact it may be more popular than many larger Cape Dory's (no offense intended, I owned a CD 28, great boats).
Fun to sail no matter your level of skill, nice cockpit for a family, pleasing to look at.
One reason I think the Typhoon endures is that it's better designed and built - especially in it's functional elements - than most peer boats of the group.
For instance, the cockpit hatches (it's stored next to my boat), have deep drain gutters, thick strong lay up and massive bronze hardware (Spartan) that looks little used after 50 years. Many boats of this size (and much larger) will be in rough condition in these areas, and much sooner.
Build quality will probably send more old glass boats to the landfill than lack of sailors wanting to own them.