If there's one thing I probably have in common with Gary Jobson, it's that I first began sailing as as a kid aboard a Barnegat Bay Sneak Box, as most every kid growing up sailing around here did back in the day. An 8-foot pram, similar to an Opti, would have been the first boat I ever sailed by myself, but all of my sailing and racing for the next 20 years would be done as crew on OPBs...
After a few years, I moved up to sailing on a Jet 14... Very nimble and tricky little boat, I definitely learned more about sailing on that boat, than any other... By high school, I was crewing on Lightnings, another wonderful boat, and the first I'd ever sailed that used a spinnaker, or had a crew more than 2. Then throughout college, I raced on E-Scows, which featured some of the most exciting and demanding sailing I'd ever done, and was my first taste of some 'Big Time' competition, traveling to regional/national regattas, and racing against some of the best sailors around...
A few years after college, I started doing some offshore racing... Looking back, by today's standards of so many jumping into big boats immediately and taking off cruising, my sailing apprenticeship was a remarkably slow progression. For almost 2 decades after I first started out, I don't believe I ever sailed aboard anything bigger than 28', or upon the ocean or out of sight of land...
At about 30, I bought the first sailboat of my own - a 16' Contender, which at the time was the first single-handed boat ever with a trapeze (Designed by an Aussie named Bob Miller, who went on to far greater fame after he changed his name to Ben Lexcen) I've had as much fun with that boat as any I'd ever sailed, but I could have retired long ago if I had a buck for every time I capsized the damn thing, and the head of the mainsail was perpetually stained by that Barnegat Bay mud...
About 20 years ago, I finally acquired a boat that I could sleep on, and actually go places with - a 30' Allied Chance 30-30... The odds are this is the boat I'm probably stuck with for the duration...