I continue not to be able to resolve this issue on OSX and have tried "Everything" (see below). It is interesting that the same macbook air can no longer sync a 4s and a 4 but can still sync an iPad. I just filed a bug with apple as below:
Summary:
After working fine for some time, I stopped being able to sync my 4S with iTunes on my Macbook Air. It sits at step 1 of 7 for 5 minutes, and then reports:
"The iPhone "..." could not be synced because the sync session failed to start."
Interestingly, my wife's iPhone 4 will also no longer sync with the same computer. Both used to work fine. However my ipad 1, also on 5.01 sync's fine. I can come up with nothing to the critical question "What changed". Not that nothing did, I just don't know what did that may be relevant.
Things tried:
Restarting iTunes
Restarting iphone.
Sync over Wifi.
Sync over USB (multiple cables)
Disable iTunes Match.
Delete iCloud account.
Resetting All settings on iphone.
Removing iTunes COMPLETELY (all library (both)) and misc settings plus hiding Backup folder.
Reinstall iTunes 10.5.1.
Upgrade iphone to 5.1 beta.
All to no avail. iTunes always fails to start the sync and eventually errors out as above.
Steps to Reproduce:
Attempt to sync iphone via wireless or USB.
Expected Results:
Should have begun sync.
Actual Results:
It sits at step 1 of 7 for 5 minutes, and then reports:
"The iPhone "Jeff Greenhut's iPhone" could not be synced because the sync session failed to start."