Re: iTunes on Lubntu
It depends on what you want iTunes to do for you. You can get the player to work with some older versions, but forget about buying music from the store - that part just wont work.
If you're looking for an online store, try Google Music. They leave iTunes for dead in terms of features, and the music costs about the same. Best part is, because it's web-based, it works across all platforms (Linux, iOS & the other one...)
Also, I wouldn't use wine1.5, as it's in development. Best to use the stable wine1.4, imho.
Best of luck!
Windows free since '09 - never looked back!