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I just took another stab at itunes with wine.. with much success!

1 – download the latest itunes

http://www.apple.com/itunes/download/

2 – install wine

sudo apt-get install wine

3 – configure wine

winecfg

-change the windows version to XP
-set up your sound card with the audio tab

4 – run (in the directory of the downloaded installer)

wine ./iTunes743Setup.exe

By no means does it run perfectly, but the functionality is there and I expect will continue to be improved.