Depending on Wine to run windows apps. is somewhat defeating the object of working with Linux. In most cases open source alternatives are available. I challenge anybody that says open source software is not up to the job and if that were their opinion then why would they be working with Linux in the first place.
Would you buy a petrol car and expect it to run on diesel ? Of course not and the same applies running windows apps. on Linux.
Your specific issue is with iTunes easily addressed using an open source alternative
Replacing iTunes on Ubuntu
http://www.psychocats.net/ubuntu/itunes
10 Linux replacements for iTunes
http://www.techrepublic.com/blog/10things/10-linux-replacements-for-itunes/450
List of open source software alternatives
http://www.debianhelp.co.uk/tools.htm
Ubuntu 11.04 (Natty Narwhal) User Guide
http://ubuntuguide.org/wiki/Ubuntu:Natty
LUg.