That's a great point. When I find things I have an interest in, or have been curious about, and they're at a great price, I snap them up, even if they're then relegated to the tall stack of things I haven't yet listened to. If I have them, I know I can. And with iTunes shuffle, I may indeed listen to a track or two at a time, sometimes with interesting juxtapositions.
As for the 22 year old with the complete Miles,
1) There was no complete Miles when I was 22. Many titles, even on Columbia, were unavailable.
2) Yes, he may have the money (or his parents' money, or maybe it was an Xmas gift). But it would cost far far far less money than when I was 22, even accounting for inflation. I'm assuming he's referring to the Complete Columbia Album Collection. It's currently $328.49 on Amazon, and it's 71 discs. That's $4.62 per disc. Even with the occasional Kind of Blue Nice Price @ $3.99, on the whole that collection would've cost a lot more on vinyl.
And he probably does boast about it at parties. Whether anyone's impressed is another story.