End User wrote:
You've not experienced pain until you've dealt with a Linux kernel update that freaks out over the installed proprietary GPU driver.
IME that one's *usually* fixable just by re-installing the driver via the text console. Back when this used to be a regular occurrence I would keep a copy of the latest driver installer in the root account's home directory, along with a script called "go" that ran the installer with appropriate options. If the DE freaked out after a kernel update, it was Ctrl-Alt-F1, log in as root, "./go", reboot, and I was back in business.
If you want some *real* pain, try using apt (or any of its GUI wrappers) to install Oracle's upstream binary VirtualBox .deb packages on an Ubuntu LTS point release (i.e. 14.04.x, where x is anything other than 0). Learned that one the hard way. There are some serious dependency issues that apt oh-so-helpfully resolves in a very wrong way, and you'll spend the rest of the evening trying to un-f*ck your X stack.