No Longer Able to Sync itunes to ipod

I recently needed to re-install Tiger. After re-installing, I ran all on-line upgrades to ensure I had the latest software for my mac. When attempting to open itunes, I was prompted to upgrade my version of QuickTime, which I did. I was then able to successfully open itunes; however, when I attempt to sync it to my ipod, I receive the message "This computer is no longer authorized to play purchased items that are on... Would you like to authorize this computer for items purchased from the itunes store?" I then click on "Authorize," and am prompted for my AppleID and password. After entering this information, I get the message "This computer is already authorized," with "Including this one, you have authorized one computer of your available 5." I click "OK" then the cycle of messages starts again. My ipod is never synced. I tried suggestions I've read on the internet and your website, trying things like "Deauthorize All" and clicking on a purchased song. All my songs have one and only account name associated with them and they are the correct name. I'm at my wits end trying to figure this out. Has anyone come up with a workable solution? TIA!

I did as you suggested. I closed itunes and ran Disk Utility, then repaired permissions. This did indeed repair permissions on a variety of apps including itunes. I then restarted my mac, opened itunes, attached my ipod (which is and has been recognized by itunes), but still experienced the same cycle of authorization errors/messages. Any other thoughts?

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