> 20+ years ago, software was so horrible that we were just tolerating it,
Absolutely not, especially not on an Apple thread.
By example, the iPod released in 2001. Anyone who used those early knows the user experience was competitive with the current experience. In 2006, I was using the version of iTunes then which was probably objectively the best desktop music app ever created. There are features then that were just there, that were pioneered, or now absent, like an automatically sorted "least listened to" playlist that are now nearly impossible to find. Sync alone is still an headache the OS community just does on the side, and no one is even bothering to compete on it anymore.
Amarok was way better than iTunes in that era. Massively better UI, separation of playback queue from collection browsing, plugin ecosystem, better metadata fetching including lyrics support... And its dynamic playlists were way more capable too.
I had an iPod in those days and Apple's firmware updates that periodically broke third-party sync (while bringing no improvements) is the reason that to this day I've never bought Apple hardware for myself from Apple since that time. Used hardware only.
Every time I had to use iTunes was regrettable. The app was an insanely massive download for the time. It tried to install fucking Safari on Windows for no reason. The UI was somehow simultaneously a sprawling mess and feature-deprived.
Maybe there was a brief period where iTunes was genuinely an interesting app, but even by the mid-aughts, it had been totally surpassed by a number of open-source music players.
But Amarok at that time was only available on Linux. I assume most iTunes fans of the time never got to try it.