I switched to Ubuntu on my main machine a few years ago. This is my second attempt. There are still some annoyances I run into, the biggest being that the dock regularly disappears after sleep. How would I ever set my parents up on something where even the most basic features require fixes like this https://leimao.github.io/blog/Ubuntu-Dock-Disappear/ ?
then you live trough your first pulse audio upgrade. or maybe you have to bring a laptop in two wireless location with slightly different network configs. or it's just a distro upgrade where the default filesystem changed and they dropped the older fs kernel module. or you have a second monitor, or a multitouch pad, and at every update there's a chance for some package change breaking their config.