Eric, I have pondered the same question many times. I also factored my skill level (lack thereof) into it, questioning whether I play well enough to have certain gear and whether I make "good enough" use of it. I have a few friends that amass gear much more compulsively and expensively than I do. That said, I think that I've come to a better place with the question. I don't spend a lot on my gear for the most part, and I do enjoy playing with it. Playing with other people makes having the gear seem more worthwhile to me -- not that playing alone in one's abode isn't worthwhile. Clearly this is a very individual matter.