I once had kind of the opposite experience: I was at a friend’s place, and we watched the recording of a System of a Down concert from a festival that we both had considered attending but didn’t. I thought it was terrific and was quite disappointed not to have attended in person. He however got to the conclusion that the whole thing was so full of flaws that he was glad he hadn’t wasted money on a ticket.
Just like you, I was baffled, and to be honest just kind of assumed he was just trying to signal his high standards or something but surely didn’t actually mean that.
Given that he was quite the musician himself, playing multiple instruments, and I’m quite the opposite, I now for the first time seriously consider whether he really did dislike that concert as much as he said.
While much of this can surely happen to varying degrees, I think an important aspect in music is also recognition (listening to the same great song you know and like many times with some anticipation), as well as sharing your appreciation of certain songs with others. E.g. when hosting parties, I usually try to create a playlist where for each guest there are a few songs in there that they will recognize and be happy to hear, because it has some connection to both of us. Similarly, couples often have this meme of “this is our song!”, which throws them back into nostalgic memories of how they first met.
None of this is to disagree with the post though. I mostly just wanted to point out that novelty and “personal fit” are just two important aspects in any person’s music listening experience, and I think it’s unlikely these two aspects will dominate the future of music that much.