One thing to keep in mind is that you don't need to buy the best of everything to get out and have a good time. "Best" may also mean different things to different people, so when evaluating something, be sure to get more than one opinion.
Buying used gear or clothes or last year's models can be good ways to save. I've written about this before, and a search should turn up some of those posts.
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Don't get me started, you know how I get.