> 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.