It also happens with my music player when playing my own library of music, it has actually gotten that bad that even random no longer works as it should.

This is why I kept all of my old CDs, Mp3s, and DVDs... One day we're going to have to boycott everything and it will be painful for those who only had subscriptions on entertainment & productivity apps.

I'll load up windows 98 if I have to! I'll do it again!

If, by painful, you mean “the need to plug in that old HDD with 100k MP3s”, keep up ratio on private trackers, and end up finding tons of amazing music again, all completely free to do anything I want with, then sure :)

Squeezebox Server was awesome, and these days it’s way easier and more accessible to host a media server and playback in ways you want.

The pain, for me at least, was in organizing all that music. I ended up with a mess of files and folders, people didn't use ID3 tags consistently (if at all) and if you need to add them yourself manually then yeah, it's a pain...

I have been saying this for years. I have a HUGE amount of CDs that I have gotten at bargain prices from thrift stores over the years (it’s been an interesting curation method), and I keep them all organized on a plex server. It’s as close to best of both worlds as you can get today imo.