I agree, that's impressive, but... every time I upgrade, and even some substantial portion of non-upgrade updates, I have to go in and fix my Grub config or else my Windows dual boot just infinite loops. That's somewhat less impressive, and it affects me much more substantially.
The more immediate usability issues mean that I have a clear divide between the OSes I prefer to use for my daily driver (OSX/Windows) vs. the OSes I prefer to use for servers (Linux). With WSL2, the virtualization capabilities are good enough that I pretty much never need to explicitly boot Linux on my laptop/desktop anymore.
Of course it's still possible that on my particular configuration it's actually Windows doing something dumb that makes grub.conf changes necessary. However, it's (1) well documented for years, (2) an issue that the Linux (distro) installer creates, and (3) an issue that still gets recreated on every update that mysteriously reverts my grub.conf changes, so Windows gets the benefit of the doubt and Linux doesn't.
That's been my experience in general with desktop Linux: I have never experienced a Linux distro where I didn't have to get into the weeds to fix up a clean install, even when Linux is the only OS on the system.
Yeah, then you reboot and find out what's really broken. About 30% of the time there's some weird problem. Last time, my Nvidia drivers weren't upgraded and my laptop's external display stopped working.
Server upgrades are usually smooth (early versions of Ubuntu being an exception.)
Sure, sometimes, maybe. But pretty much only if you've only ever used software from the main repo and of course not anything they've dropped between versions. I've had plenty of Linux upgrades break stuff. Not just programs, but core functionality. Linux Desktop has pretty much the opposite compatibility story to Windows.
Shit! I was playing Stellaris meanwhile I was updating to Kubuntu 18.10