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Original poster
I've tried to delete backups from the iTunes Preferences, but nothing's there. I've checked the Backup folder in the ~/Music/iTunes but it's empty. I've replaced iTunes cache files and plist files from ~/Library/Preferences. I've gone through multiple iTunes updates and OS X updates, and nothing fixes it. It's been months now. Everything else works regarding syncing.

Please help, really want to taste that iOS 5 iCloudy goodness. 😛
 
ISSUE RESOLVED:

When deleting iTunes through terminal and reinstalling didn't work, I went through Application Support and realized there was a backup folder in Mobile Sync. Trashed it and it is now backing up.

For those having this issue: DELETE ~/Library/Application Support/MobileSync/Backup/
 
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