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.
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.
When it comes to the software, I’d take the Tiger experience over the Tahoe one hands-down.
I don't think software is improving today, which is why I have to be nagged to upgrade. I don't think it worse, but my computer usage probably varies greatly from yours.
I understood that, and I was using it in the same way.
> I don't think software is improving today, which is why I have to be nagged to upgrade. I don't think it worse…
Yeah this is the part I was disagreeing with, and I gave a couple examples showing why it’s meaningfully worse now.
I’ve been using Macs since the 1980s. The timeframe of 20-25 years ago (post Classic Mac OS) was some of the best software Apple has ever released.
The macOS Tahoe release is a great example of this. I can't think of a single thing I prefer about it and could easily name ten things I hate about it.