This just occurred to me so I felt I had to put it in writing!
After getting my new bike, I've realized how unhappy I was on my previous bike. She was certainly beautiful and definitely cool to look at. However, it didn't fit me right. I managed to ride it for a couple years and I even took it to LA a couple times. I think I was forcing myself to like it, even though deep down I really didn't.
It was a little too top heavy, a little wider/fatter around the engine, and the suspension was horrible. I didn't enjoy riding nearly as much as I do now. Going on rides was something I theoretically wanted to do, but never did because I knew that I'd have to put 20lbs of weights in my tailbag to stabilize the rear suspension. How fun is that? NOT fun at all! To me, it really felt more like work than fun.
Riding the SV feels right to me, everything works for me and my body, and my riding style. It just fits me. Now I actually want to ride, any excuse to ride and I'll do it.
I think the same goes for your gear. If you buy something that doesn't fit you quite right or isn't the right type of gear for your riding style, you probably won't appreciate it for what is, and you might not even wear it all the time. Why would you? If your gear isn't working for you, or doing what you need it to do, it'll make it really hard for you to justify spending the money on a better piece of gear next time. I think it changes the way you look at gear and why it's worth spending so much $$ on.