I am a Squeezebox owner, but alas, not an iTunes user. Check the Slim Devices wiki first: http://wiki.slimdevices.com/index.cgi?BeginnersGuideToiTunes

Then, you may want to go to the plug-ins page to see if there are any 3rd party solutions: http://wiki.slimdevices.com/index.cgi?PluginsAudio
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Outlaw 970
McCormack DNA-125 (mains), Emotiva LPA-1 (surrounds)
Quad 11L (F&C) Wharfedale (R) LFM1 (Sub) w/ SMS-1
Squeezebox -> Behringer SRC2496 -> Musiland MD10 DAC
Sota Sapphire; Marantz 10B;
Video: Hitachi 42HDS52A; Oppo 971H
System Pics