The thing is, now I don't know why I did it. I must have spent a fortune on replacement pick-ups back then: Seymour Duncan, DiMarzio, Paul Reed Smith – all these guys are richer because of me. I was looking for something, but I'm not quite sure what because my experience since then has taught me that a good player can get a good sound out of even the most average instrument. It's not the gear, it's the player, after all.
I sometimes see it in students I've taught, though; that idea that if they could get hold of a very expensive instrument, effects unit or amplifier then all their problems would somehow go away. After all, isn't it easier to play great blues guitar on a great blues guitar? The answer, in case you're wondering, is 'no'; it's certainly no easier, but it's arguably more pleasurable and I think that's the answer to the whole conundrum. We invest more in peripherals or changing instruments because of the way it makes us feel as opposed to the way it makes us play.
So if walking on stage with a vintage Strat makes you feel better about being there and has the knock-on effect of making you play better then it's worth the investment. But it's a heck of a lot cheaper to adopt the mindset that the majority of your investment ought to be directed at your playing, rather than your gear!