The latest XBMC has the possibility to stream music from iTunes servers on the network. I do use iTunes, but I think J. Rivers Media Center (version 10) is a much better media player for the PC
Is it possible to stream music from this Media Center to the XBox? Media Center 10 has server capabilities (with TiVo HMO support, whatever that means).
You can find J. Rivers Media Center at J. River Media Center 10
Kind regards,
Erwin