You can’t hit the target until you know where it is.
When I was a freshman at college, this clever upperclassman would try to get us new frosh to over-consume beers at parties by saying, "You can't know where the line is unless you go over it." Then, once someone was beyond holding their liquor, he'd direct them to go throw up on Ware House, the dorm for all the pre-med students in our complex. Just a fun memory, since I wasn't the one who threw up.
As for audio, I have recently heard some very good systems, but not in the stratospheric range. A couple of them had custom builds happening, so it's hard to know what they cost. What was true, though, was the the owners had really worked for years on them, and what I was listening to -- whatever the sticker price of the gear was -- was the result of a lot of sweat equity, true audiophiles who listened, tweaked, changed gear, listened more, worked on room acoustics, etc.
To me, the question becomes akin to the difference between the experience in a cozy, comfortable, home which has been domesticated with love over many years vs. a new, expensive, super modern house. One of them is very expensive, and some great features; the other is humble but crafted into the site of aesthetic experience. I cannot see how price plays a role in that kind of comparison.