I'm in the process of trying to keep several ubuntu box's up to date and patched (10.4.2 LTS), one suggestion I've been getting is setting up unattended upgrades (https://help.ubuntu.com/community/AutomaticSecurityUpdates).
In the past I've been against setting up automatic updates, mainly due to paranoia that it will break something during the update process. However now I'm starting to question how valid this is (and how much of a risk it is compared to having potentially unpatched servers). Is this a sane idea?
We are also in the process of setting up Puppet, however the creation of modules/migration of servers to puppet seems a long way away.