First thing you could try is starting out with a clean prefix. If you don't have any other important programs installed in wine, you could just remove ~/.wine. More information about that here: http://wiki.winehq.org/FAQ#head-9893ae50079ca7a959258f0bc9a17aaf2e69b391 Also, if you're trying to sync your iPod/iPhone with iTunes. That won't work. But there are other ways in linux to do that, and there are also great alternatives for playing music.
