I need to come by and check out y'alls Community Sailing Center. This place needs something like that.... in fact, IMHO most small coastal towns doIf "owned" means paid for it, then my Turnabout doesn't count, parents bought it when I was 9 or so.
In that case, an elderly 110 built by Lawley Brothers, raced it during high school off Marblehead. Got crushed by the Doyle brothers, among many others. But it was a fun Ray Hunt speedster for a teenager, and I learned how to race slow and semi-clueless, which later on helped me learn to sail fast by doing the opposite.
Next was a fiberglass 16' Marblehead Town Class, big main small jib lapstrake half-dory. Big racing fleet around New England, particularly Marblehead. The newer glass boats weren't as fast as the older woodies. So I sold her and bought an old but not too old wood one. Gradually improved and started winning. There were four races per week in Summer, so you could sail you ass off--Tues and Thurs evening races from a fixed starting line off the Corinthian YC, then Sat afternoon outside with a committee boat, and Sunday morning races off the Corinthian.
The Townie "nationals" meant a couple of boats from NH and RI joined us. I won it one year, just before moving south to New Orleans.
Aside from that, it's been OPBC for me, from college dinghy racing and coaching at BU, to crewing MORC, and doing a few deliveries around eastern New England. And borrowing and racing boats down here, and teaching sailing for an ASA facility, and now at our new Community Sailing Center.
Whew. That's probably a lot more than you needed to know. I've been lucky to sail mostly on the cheap.