I remember enjoying using Windows 2000/XP but I feel like that's my nostalgia talking. I was customizing a new installation for days, messing with registry keys and obscure settings dialogs. It was never that user-friendly to begin with. After having used MacOS for the last few years, I do not miss the hassle.

To be fair, not a lot of things were user-friendly back then, and Windows was the standard consumer OS for a good reason. It was solidly OKAY.

Using the latest versions of Windows, however, is just infuriating even without any complicated setup.

Absolutely not your nostalgia talking.

I’m as OS agnostic as they come and Win2k was the last true great desktop OS.

I now use FreeBSD almost exclusively, with miscellaneous VM guests.

I grew up with an Apple II, then switched to Windows from 3.11 for Workgroups all the way up to Vista, at which point I switched to desktop Linux (variety of distros, but mostly ended up on Kubuntu in my house and Mint for family). Then it was 8 years of ChromeOS. The past couple of years I've been on MacBooks and, although there are quirks I don't really like, I can't argue with the fact that it mostly "just works", which is really the primary requirement of any operating system.

Still, I would say peak Win2k was faster, cleaner and more no nonsense than modern MacOS. I use macs as well, they are not at all as snappy as windows 2000 was.

I actually REALLY LIKE MacOS, especially workspace/window management when using Rectangles. So much so that I'm trying to recreate it on Linux (I don't want to buy a new Mac when I have a perfectly good gaming desktop to repurpose for dev work).

MacOS is pretty good, can’t argue with you there.