Kaleidescape is about to ship a new version of its software for all owners that includes synchronizing ones music collection into iTunes.

The server handles all transcoding into MP3 formats (your choice of bitrate), and the integration is very nicely done. All meta data migrates to iTunes and onto iPods including cover art. Slick.

Details and screenshots posted on Kaleidescape Forums:
http://www.kscapeowners.com/forums/forumdisplay.php?f=5

--josh