I'm 27 now, and got into sailing about 4 years ago after visiting a friend of mine who had a Club 420. I bartered for a Sunfish the following summer, took a sailing class, and my wife and I recently upgraded to an 18' sailboat 30+ years older than we are.
This is our first year having the boat at the harbor instead of trailering, and it's been nice but I do miss having the boat in the garage if I want to tinker with it. I don't miss the 3-4 hour rigging time before launch, though.
~Matt