>If 512M is not enough space for /boot you're doing something wrong.
I don't know what planet you're living on but it's certainly not this one. Between a Ubuntu desktop, a laptop and personal server with multiple Ubuntu VM's on it, all of which are kept up rigorously to date, I fix this problem at least three times a year, every year.
The command line process to fix it[1] is a multi-stage mess of dense bash-foo that comes with a 140 word, two paragraph explanation so that /ubuntu veterans/ can figure out what is going on without resorting to scouring the man page for flags. The friendly GUI process to fix it relies on a third party tool that is no longer maintained[2].
It is not possible to explain to non-technical users what is happening here, which means the only thing they can do when they see this is call their technical friend and cry for help. This is exactly the kind of user experience that makes people think Linux is not ready for widespread desktop use.
This is definitely something the OS should take care of itself. I'm ignorant of the challenges that caused it to be this way in the first place, but in my ignorance I would advocate that:
a) the partition be made larger by default
b) the OS auto-purge any kernel package more than three revisions old
[1] https://askubuntu.com/questions/89710/how-do-i-free-up-more-...
[2] https://launchpad.net/ubuntu-tweak/