My first PC was a 16K color computer in 1982; used a TV and a tape deck. I've still got it. After that, I built my PCs because it was a lot cheaper. I built at least 10 of them for the wife and I. Then maybe 10 or 15 years ago or so it became cheaper to buy them built. But in all of that time, from DOS, through Windows 1.0 and on down I've never had a problem that I can recall with operating system updates. Maybe that's because I learned very early on not to fuck with your computer. Back when everyone was overlocking, I wasn't. When people were dicking with driver settings, I wasn't. And I just never had a problem.
Now I did have problems with graphics over the years which taught me to never upgrade video drivers; if they weren't broke, I didn't fix them.