this issue isn't new and has been around ever since I updated iTunes to 7.7.x
I had 1.1.4 and iTunes 7.5 and syncing couldn't go any smoother.
I updated to 7.7.0 and it was hell. I asked and everyone said to uninstall and then install iTunes, uninstall the apple mobile device and so on. That's what I did - it didn't work.
Then I updated to 7.7.1. The first few times, it didn't work. Then I updated my iPhone to 2.0.1 (custom firmware and all). Sync started to work suddenly - until last week.
So I had to switch on: manually manage songs and videos in order to have iTunes not hang when I pressed the sync button.
So I updated to 2.0.2 and quickpwned it (only jailbreak - didn't install Cydia or Installer [although I did try it with those a couple of times]) and it still doesn't work. Whenever I remove the option to manually manage my media and I press sync, the iPhone backs up rather quickly (takes less than a minute), syncs contacts and calendar events and when it says: syncing [iPhone's name] after having finished with the calendar part, the sync just freezes and iTunes hangs.
To close it down, I have to right click on its tab (because everything about it stops to respond) and click delete. A program non-responding thing pops up and I have to click end now.
Then another window giving me the option to notify Windows or close the program anyway appears. (It has the problem details which are always ApphangB1).
I tried to uninstall it, then go back to 7.7.0 but it didn't work, then I updated back again. I even repaired the Apple Mobile device, but to no avail. I have no idea why it's doing so and apple support didn't even reply.
I need help!!! My music is out of order with this manually manage thing: mixed up artwork, things get deleted here and there.. no idea how!
Just today, I was had to go somewhere and I was searching for Carrie Underwood's Some Hearts Album. I could only find one song; I DON'T EVER DELETE Carrie Underwood songs because she's my favorite artist.
So I don't know what's happening.
PS: This is a bit long because im trying to give as many information as possible.