I upgraded Linux Mint to version 20 and it just worked. Desktop linux went a long way since I was using early versions of Debian.

I don't remember when an upgrade caused issues (except for audio driver ones)

I once upgraded my ubuntu 14 to ubuntu 18, and everything went ok until virtualbox got in the mix. The upgrade shit itself with some mad vbox error and the upgrade failed. after restart it was running 18.04, but audio and the entire login screen was fucked and unresponsive.

I did a clean reinstall, since its pretty easy with linux anyway, but it left a sour taste in my mouth

@shakur you must've responded to the wrong person. I wasn't talking about gaming nor hard drives, hmm :|