Don
I've found ubuntu generally does a rubbish job at cleaning up /boot, i regularly have to manually remove old kernels from /boot before running 'apt-get -f install' or the 'dpkg reconfigure' command (i forget the syntax).apt autoremove ? Always did the trick for me in previous versions, no grub editing needed.
dpkg -l | grep 'ii linux-image\|ii linux-headers\|ii linux-modules\|ii linux-tools' | cut -d ' ' -f3 | grep -v `uname -r | cut -d '-' -f1-2` | grep '[0-9]' > oldKernels && sudo apt remove `cat oldKernels`
I found that it is far easier to abandon the small partition and move /boot to the root. This also prevents any out of space issues in the future.
First move your data from the boot partition to root (run as sudo -s):
cp -a /boot /boot2
umount /boot
rmdir /boot
mv /boot2 /boot
Remove (or comment) the /boot entry in /etc/fstab:
vim /etc/fstab
Update grub and make sure everything is correct:
update-grub
apt should now be able to upgrade without problems.
This leaves an unused 200mb partition (which you could use for something else if you find it worth the trouble).