I don’t know but for some reason I am completely disappointed by the whole Apple on Windows experience. I really thing believe that iTunes for windows is a really heavy application, and it misses too many features… No library management features. For example I would like to have iTunes checking my custom folder for new tracks, or if I for some reason change many track tags, to be able to rescan by entire library for changes. I am kind of able to do some of that things with some third party applications but it isn’t such a great solution after all. And actually the only single reason that I use iTunes is to sync my iPod. Not that there aren’t other applications that can do the same thing, but the last great looking solution I tried, within Winamp, that supported iPod scrobbling, because I want to get whatever I listen on iPod up to my last.fm profile, lacked Unicode support, so it messed up all my Japanese/Chinese/Korean tagged mp3 on my iPod.
The greatest problem lately seems to lie within iTunes 9. When i upgraded from version 8 to 9, for some weird reason all my library on the iPod got corrupted… I had a while since I last used my iPod, so I get ready to leave my home to go pay some bills, and I pick my iPod cause I want to listen to some music while walking and while waiting on the queue to pay the bills, so I get out of my home and try to listen to some music, I can see the cover art displayed in the menu’s right part, but when I try to listen to some music, it seems that my iPod is empty!!!! So I had to restore it when I got back at home.
My latest issue with iTunes is with 9.0.2 deleting the track play count on iPod. Before the sync the Recently Played smartlist on iPod had 18 tracks that I listened to while away from home, and in the iTunes the same playlist is blank, no tracks at all. So as soon as I get back I do a final check of the playlists just in case and i connect my iPod in order to sync it. Well the result of the sync is that all the plays on the iPod are gone… and the recent played list is completely empty like it was on the iTunes, and none of the tracks I listened while on the go had their play count updated.