Ran a couple of Xserves a while ago to run web application stacks on it and most of the time I diverged from using the GUI to administer things I shot myself in the foot (Apache, firewalls, initscripts, networking etc.).
The nice hardware - those CPU load meters were gorgeous - unfortunately doesn't make up for those problems so I switched back to non Apple hardware + Linux and never looked back.
Don't fight the system is a nice mantra to follow when using Mac OS X Server and that's not hard when you use it to administer a collection of other Macs & the network they're on or when using the built-in services without wanting to tweak/upgrade the versions yourself (iCal server, Mail server etc.).