For me personally, it's all about the music. Good music is music that moves you no matter what gear it's playing on. One of the most profound experiences in my life was the first time I heard my favourite song - in a store, on the radio, playing out of a tinny mono speaker - pretty much the crappiest audio quality scenario possible. Yet it was enough to restore my faith in humanity. That's real music.
On the other hand there is crappy but well-recorded music that only sounds good on high end equipment. I must admit that I've been guilty of thinking "hey, this actually sounds pretty good, for once" when playing boring music-- tracks that I would normally skip--on my decent gear. That doesn't make it good music, but music is meant to be enjoyed, and if nice gear helps me to expand/increase my enjoyment of music that I wouldn't normally enjoy, that's never a bad thing.