1 - What is you intended use for the boat you're looking for? Are you simply wanting to learn how to sail a cat at this point with the idea of eventually going racing, or do you want to jump into racing as soon as you can? In other words what is your perceived timetable for getting into racing if you want to race? Or, do you really want to race at all?
2 - Are looking for a crewed (2-person) boat, or are you looking for something that you can easily handle/race on your own, maybe taking an occasional passenger along for a ride? Do you have access to readily available and willing crew?
3 - If you want to race, do you have an opinion on whether you want to go one-design (everybody on the same boat, first over the line wins) or run-what-you-brung (handicap, math decides winner, not all the boats the same)?
4 - You're saving money for the purchase, but how much do you envision having available to get started?
#1. My first objective is to learn... not to race. What I liked most about kayaking was doing something difficult well. I liked to push myself to refine my 'art'. I like to take something challenging and work it until it 'looks' easy. Most of that is very personal and has little to do with anyone else on the water. I think that at some point, competition is the best way to personally develop in your sport. Racing is a natural progression but not a goal.
#2 I want to be able to have crew but I DO NOT want to have to depend on it. I have always chosen sports that were solo. (Biking, rollerblading, kayaking) That way, I can just grab my gear and go.
#3 One design
#4 Around $2,000 for just the boat. I expect to have to spend that much again for trailer, wheels, gear and so forth. That will still leave me a bit in the bank to fix/upgrade stuff if I need to. So $5,000
