Is an update from 14.04 painless or would you recommend reinstalling? I'd like some newer packages but don't really feel like setting up the whole system again with a reinstall.
If you don't feel a particular urge to upgrade right now, it's probably not a bad idea to wait for the first service pack (16.04.1), which usually comes a few months later. Most kinks should be ironed out by then.
Pretty painless - I've just ran this on two servers (not in production):
sudo do-release-upgrade
or if you're on a server
sudo do-release-upgrade -d
although they don't recommend doing that on a production server because the .1 release usually has a lot of bugfixes.
It took about half an hour followed by a reboot. Occasionally had to intervene to tell it to overwrite config files I hadn't touched or to let me do a merge if I had.
I always wait a month before upgrading/reinstalling. I have done upgrades in the past through multiple versions and they generally go smoothly but there might a minor glitch or two that requires manual intervention to fix (usually solved though search google for advice.)
Another thing I've done is keep /home on a separate partition so I can nuke everything else for a clean install if needed. In such cases, I backup the /etc directory beforehand to recover configuration details as needed.
