I forget how much I love the Linux movement sometimes...
We have several servers (Windows and Linux) here and keeping them up to date is a pretty easy process. We had few Ubuntu 6.06LTS servers that needed to get upgraded to 8.04LTS. In the Microsoft Windows world, that would entail a complete reinstall wasting countless hours/days. In the Linux world I just did the following on the Ubuntu 6.06LTS boxes (as sudo of course)...
1.) lsb_release -a
2.) apt-get install update-manager-core
3.) do-release-upgrade
It literally, took 20 minutes to do 4 machines! This was awesome! Can you imagine upgrading 4 Windows 2003 machines to Windows 2008 like that? I wish!