so many people, so much idiosyncrasy.
Jay,when I was reading your post, I wasn't thinking the word 'anal' that you used, but I did think I'd use 'picky' in my reply. Here you go: this makes me think you are
picky 
Well my woman tells me that I'm picky to some detail (which means: in rare cases when I'm really interested). Like last night, I re-did the copper shielding on my 55-JJ because I didn't like what it looked like

or, like the other day, Doug AKA Basspraiser (whose signature reads 'Lakland Addict') called ME a Lakland geek, LOL, for thorough description of differences between Lakland USA and Skyline.
Well anyway, like you, I've always earned all of my gear. It is true that those were the first POS guitar and bass that my dad brought home; but, firstly, it was because
he had played in a school band and he was interested; secondly, that stuff was total crap and I didn't play them a week.
I've bought stuff new and old. In fact, I tried to buy new stuff since I thought it could make me feel cool. The truth was, it didn't, and I realized I'd spent money for nothing. Also, that trying to keep the thing look untouched is too freaking embarassing. New became old anyway and that's the nature of things.
So instead, I try to get awesome used stuff at great price. I also try to stay away solid black finishes because they work as a fingerprint pad, especially under the stage lights. True, I had it on 2 of my Laklands, 1 brand new from the factory, but I got them at a steal of price. Actually, the new one is a B-stock with a dent on that can't be seen unless yo're inspecting the edge of the headstock, and I got it for the price of a used bass.
The bottomline? My stuff is for playing. True, getting the first scratch, whether on my bass or car (rather expensive one, but I got it for a steal of a price) does piss me off. Man, right now a window is broken by some punk, and I just received a spare part from Moscow that longed for two weeks. But, really, jerking
each time I get scratches would disturb me from playing, driving, and, finally, living.