excelent thread. We've all been where your at looking at our first used boat. All suggestions have been insightful, but my rule for old boats ( I just bought my 11th last nite is ideally spend 500 or less then put 5-10 times that into it <img src="http://www.catsailor.com/forums/images/graemlins/smile.gif" alt="" />. Seriously if you were staying put might be worth your effort but you better have a fare Amount of free time, a tolerant wife and some spare change. The other thought that hasn't been brought up is racing. Racing is the best way to get better at sailing fastest. The chance of your finding other super 17s to race against is slim to none. The is only 1 super 17 I know of in Florida. I would try to get hold of the local cat fleet in chicago and see what kind of boats are showing at their regattas then target on those. Hobie 16s are universal and likely best ba g for the buck all round. Hobie waves are also real fun in medium to heavy wind and fairly bombproof and great solo boats, but are usually 4 k new and not much less used. Whatever you do however, you'll be psyched and think its worth it the first moment you fly a hull on a nice close reach.