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> 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.

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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.

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I was using (and writing) software as long as 35+ years ago and I disagree with your assessment that we were “just tolerating it” 20 years ago. 20 years ago, I was using Mac OS X Tiger on a new Intel-based MacBook Pro and it ran like a dream, and had software which mostly followed Apple’s human interface guidelines. Now I run macOS Tahoe and curse under my breath at the lack of design consistency and the iPad-ification of the interface. I’m also shown ads, and in some cases ads that can’t be dismissed or disabled, for things like iCloud and Apple Music.

When it comes to the software, I’d take the Tiger experience over the Tahoe one hands-down.

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I used 20+ years ago as a guideline, not an absolute. Of course the intel MBP came out in 2006 (or 2007?) and was an absolute dream setup where hardware caught up with Windows while the software was pretty good as well (I was using a Mac since 2004 or so).

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.

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> I used 20+ years ago as a guideline, not an absolute.

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.

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Maybe. I personally couldn’t afford to switch until 2004. And I grew up with PCs (well my first computer was an Osborne). Even then, it felt expensive and slow until the Intel switch.
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Same here. Two decades ago, I was excited to install updates to commercial software I used because they fixed bugs and brought useful new features. These days I fear updates because they introduce new bugs, remove features I care about, and come with new anti-features that I actively do not want.

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.

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