Solution: iTunes 10.6.0.40 on Windows 7 hangs while syncing
I was trying to Sync Audiobooks to my iPod nano (6th gen) but iTunes 10.6.0.40 (on Win 7 Home Premium 64-bit SP 1) just stopped being responsive after pressing Apply and it showing "preparing to sync" in the status window. The nano went into sync mode for about 5 seconds but then returned to Connected state. iTunes.exe *32 was running at 100% (on one CPU) and did not even appear to begin the sync. [This state was also entered as soon as I set the "Manually manage music and videos" on the Device's Summary page.]
After (wasting) many hours of trying the standard support instructions to uninstall everything from Apple Inc. - iTunes, then Apple Software Update, then Bonjour, then Apple Mobile Device Support, then Apple Application Support - then download (another) copy of iTunes64Setup.exe, then install iTunes - the answer came ...
A very pleasant, helpful support rep (for case 298676734) thought to try the DOS command "netsh winsock reset" as suggested by wiclee in https://discussions.apple.com/thread/3559328 and sodaboy581 in https://discussions.apple.com/thread/3383758. More explanation of this fix can be found at What does "netsh winsock reset" do? and Repair/Reset Winsock settings.
I suggest you try this first!! 😉 Hopefully this discussion has enough fo the right tags to help others find this fix!
iPod nano (6th generation), Windows 7, iTunes 10.6.0.40