I am responsible for setting up a large number of specialised boxes. By this I mean mail servers, network management servers, etc. I find that keeping these machines up to date can be a daunting task. This is further compounded when the organisation does not have any Linux skills. To help wit this problem I tend to set up APT-GET or YUM to track Dag Wieers RPM repository. Most of the staff have been educated to install packages from the repsoitory using SYNAPTIC or similar tool. As a result updates are handled more or less automatically.
The repsoitory can be found at http://dag.wieers.com/home-made/apt/
It should be noted that this does NOT result in a set and forget server as some updates change the configuration files, this results in manual intervention. YOU DID MAKE A BACKUP DIDN'T YOU :)