Funny you should ask? About 3 years ago I won a fishing kayak. Being that both my wife and I love to fish, I sold the kayak, and bought a pelican 16' square stearn canoe. Then I bought a used little 4hp motor. Well if your fishin for more than 3 hours sittin in a canoe ain't the most comfortable thing, especially if your in your older years. So I sold the canoe, and got a little 14' starcraft row boat. (I guess you can see where this is going). Well last year my wife and I discovered Taylors Island M.D. and the chessy bay. Well the little starcraft was to little for safe boating on the chessy, so last fall I had to buy a bigger boat. (I swear this is my last!!!!!) So now I am deeper in debt and came a long way into the money pit from winning a Kayak. Am I sorry? Well not really, as both my wife and I rediscovered tent camping and roughing it. Love them Chessy croakers.
SO the moral of this story is go for what you think you will be happy with, and think of your future.