I broke Arch when they switched to Systemd (the process that launches all other processes), and that's because I was an idiot and partially applied the fixes without rebooting, so things got borked. I could've fixed it, but reinstalling was faster (like 30 min, and I kept my files; fixing could've taken a couple hours).

Other than that, I've had a couple drivers get misconfigured or something when upgrading Ubuntu or Fedora (I've had wifi and sound fixes not apply to an upgraded version), but I've never had an upgrade actually fail, and fixing it usually only took an hour or so to find someone online who has already provided the config options needed.

So yeah, I've had nothing like this on Linux in the 15 or so years I've used it, everything so far has been fixable with relatively minimal effort. Then again, I don't use any fancy licensed software, so I haven't needed to pull an old version of something along across multiple releases (almost got a Scrivener license, which no longer supports Linux).