For some background, I grew up on Long Island sailing on some friends' boats here and there. Never could afford to keep my own boat in the water and never got into racing small dinghy or the like. Parents bought a lakehouse in Pennsylvania with free docking in front of our house, so I bought an O'Day 222 to putz around the lake. I like sailing it so much that I want to buy a trailerable dinghy that I can single hand on the Great South Bay and sometimes the Sound here on Long Island. I'd like to be able to bring friends along, and I'd like to enter some beer can races here and there with friends.
I found a very good deal on an Islands 17, which is basically a Tanzer 16 copy. It is in very good condition, comes with very nice trailer, and has all the fixings and lots of little updates (cam cleets, new running and standing rigging, etc) - even has a 2.3 outboard that I can sell for extra cash if I wanted. Only thing it's missing is a spinnaker.
Am I wasting my time with this boat or should I save up for something like a Flying Scot? My worry is that I get this boat and it's just too much of a day sailer and not fast enough to have fun single handing. My other worry is that the boat is so obscure that 1) there's no handicap ratings really available for it for beer can racing and 2) there's no off the shelf parts available obviously.