Windows gets a big update every few months. Those would always fail for me because I had a custom partition layout (Hackintosh) and I would have to reinstall every time.
Popups? Maybe he means the new notification system that was included with... 8? I hate notifications that cover part of my screen while I use my computer/mobile, so I have them disabled. I can understand that they are annoying for some, and they are not trivial to completely disable.
I mean, yes, there popups. But my linux installation does exactly that too, every login I get software update popup by default and if I don't want to see it I need to change options manually (and update settings in linux are far from trivial).
As for bad upgrades - I had linux upgrades which failed something in the video path and I was stuck with broken X server and no GUI. And I didn't manage to repair that state even after extensive searching on stack exchange, so I just deleted everything and reinstalled. Another time I tried to install custom software and ended in a error hell of incompatible versions of libc, libtrpc etc. and it simply didn't work (it was on Debian), but at the same it worked just fine on another VM with different distributive.
Popups? Maybe he means the new notification system that was included with... 8? I hate notifications that cover part of my screen while I use my computer/mobile, so I have them disabled. I can understand that they are annoying for some, and they are not trivial to completely disable.