I have been enjoying this song for more than 10 years now, and I couldn't agree more every time I watch the video.
Last month I got stuck for 2 hours on a client site, just following a regular Windows 10 update.
And the latest, three (yes, 3) days from a factory reset on a Windows 7 laptop to upgrading to Windows 10.
Not that painful, but noticeable bothersome it's an update in my Ubuntu Linux box, and kind of the same in a Mac notebook (Linux-based, BTW).
However, there is still some hope when upgrading my Chromebook laptop, that is my main computer since last April
The Chrome OS update just take a normal restart (about 10 seconds) to complete, that's it, just a normal restart.
I guess this is possible because the Chrome OS is a minimal hardware-optimized Linux version, running a single though powerful application: the Chrome browser, with everything else within.
So, while Google keeps the OS that way, there is hope that almost every OS sucks, but the Chrome OS.