After a fair amount of fiddling with different options last year I finally settled for a TwonkyMedia server running on Ubuntu on an old (and I do mean old) PC as a basic media server solution. The addition of Grip set to auto-rip inserted CDs made adding media fairly easy as well. This setup worked ok most of the time, though it had a tendency to fall apart at the seems at the precise moment I actually wanted to show guests how cool it was to have all my music served up to my '360 for easy use, and these hiccups seemed to become more and more frequent, to the point where we just started using CDs again instead.
Having recently taken the plunge and switched my home laptop entirely to the latest Ubuntu version (8.10) and tried the Xubuntu and Kubuntu flavours as well, I thought the much zippier Xubuntu would make a great choice for a reinstalled media server. The actual Xubuntu install off the Live CD went perfectly of course (if a bit slowly), but from there things pretty much went pear shaped. Xubuntu doesn't include samba sharing or a remote desktop server by default, the only two requirements I actually have for managing the server (and I don't have a decent connection at home to get these components). Twonky itself also refused to run for no apparently good reason, no matter how many times I uninstalled, reinstalled and tweaked it.
Seeing that XBMC (previously Xbox Media Center) was now available as a Live install (and as an install for Linux, Windows and Mac), I thought I'd give that a try instead. The Live CD ran, though very slowly, but once installed I ran into more problems.
I did start trying to track down solutions to some of these issues, but just can't be bothered to keep at it any more. This is why Linux still isn't ready for the average user. XBMC did really impress me though, and I decided that since Microsoft is no longer even selling games for the original Xbox (except as emulated downloads on the '360) I may as well mod my old Xbox and enjoy the swishy goodness of XBMC as it was intended to be used.