I tried iTunes in Wine again today to follow up to my optimistic post back in 2007. Unfortunately, I would say I did not have much luck. The installer did work well, and the application did launch. I had the program lock up almost immediately, and had no luck finding a workaround.
I’m sure that every time the Wine developers make an improvement, Apple throws in some more tricky code. As it is now it’s not working well enough to use on a regular basis, but much of the key functionality is there.