My father was a hifi junkie. . . read all the magazines, saved up and upgraded his components over the years, and made the rest of the family help him do blind hardware comparisons. The result was that he had highly trained ears and could really tell the difference between these things. But I do wonder if all he really achieved was making himself more fussy.
I think for him the best possible sound experience would have been some mythical perfect set of stereo equipment that would reproduce every last nuance as if the whole band we right there in front of him. I tend to think that a good rock song can always be enhanced by the roar of a V8 and the smile of the girl sitting next to me (at least this is how I imagine it working.)
I suspect I probably love music as much as he did, but I can enjoy it through relatively cheap headphones and whatever my current phone is. I think he was so in love with the idea of reproducing it with maximum fidelity, of hearing every last instrument and sound, that maybe it became more of a technical exercise than anything else. I try to make sure than I don't get too interested in perfect sound reproduction, as I worry it will only hamper my enjoyment in the long run.
And in any case, he left me his stack of Cyrus kit and PMC speakers, I'm good.