What works

Compiled wine 1.3.1 from source, performed iTunes 8.2.1.6 install with defaults accepted except:

+ Unclicked "Use iTunes as the default player for audio files"
+ Unclicked "Automatically update iTunes and other Apple software"
+"AutoRun is turned off. iTunes won't be able to recognize when a CD is
inserted or ejected until your computer's AutoRun setting is turned on. Do you
want iTunes to turn on AutoRun for you?" No

Upon seemingly successful install, ran for first time:

+ Unclicked "Add MP3 and AAC files"
+ Choose "Yes, keep my iTunes Media Folder organized"
+ Dialog box noting, "Warning! iTunes was not properly installed. If you wish
to import or burn CDs, you need to reinstall iTunes."

I could navigate around the iTunes Store and the first time I tried to subscribe to a free podcast I got a dialog box noting, "We could not complete your iTunes Store request. The requested resource was not found. There was an error in the iTunes Store. Please try again later." However, I tried again on couple different podcasts and finally it would download.

What does not
When I tried to play a video in an external iTunes window, I heard the audio but did not see the video.

What was not tested
Everything else.

Additional Comments

This runs the best so far among the versions I have tested for my simple purpose of easily and automatically downloading subscribed podcasts simultaneously. However, at this point in Wine development, I would not use iTunes for anything else but that. As well, be cautious as to which version of iTunes you use, one peek into the bug list and you will know it does matter!!!