I'm sad to admit Led Zeppelin has lost some of it's charm after many listening, which makes me sad because I enjoyed it so much in the past. I've found a lot of Pink Floyd stuff is complex enough that I'm still enjoying it and noticing new things after many decades of listening to it. Watching videos of Floyd playing live also opened up a whole new appreciation for the music.
Lots of the music I enjoyed as a kid/teenager had themes I can only now understand in my late 30s, and didn't really appreciate or fully grasp back then.
Overall, a lot of prog really seems to have enough complexity to remain interesting for a long time. Most of Tools albums, I seem to not enjoy much at first, but enjoy more, and notice more things each time I listen, even after hundreds of listens.
The same music that is complex enough to remain interesting over time, usually doesn't compress well and is really damaged as a low bitrate MP3. I've found those same albums I listen to most year after year are the ones I sought out lossless versions of.
Even on crappy old junk headphones, still an awesome song that I don't think I'll ever get tired of.
Granted, I don't generally let services make a playlist for me, and I don't beat the old songs to death. I like more variety than that.
I have however, rolled my eyes when listening to services that have an "80's rock" or "top 90's songs" only to have them play the exact same dozen-or-so songs that they did the last time I visited that channel. No thanks!
That's also probably one of the reasons I rarely listen using a service-generated playlist/channel. I think they are maximized for the service's profit, not for the listener's enjoyment.
I’m not really interested in reliving that time.
If you can risk a 101st time, have you tried "Dark Side of the Moonshine" (2009) yet?
Sometimes I forget their version of Breathe isn't the original.