Old Purchases not syncing with Not Authorized Errors

Help --
I have had an iOS device and iTunes for over 7 years and have made a number of purchases.  This was working fine up until this week.  Only change was I deleted an old user account from a family member from the MBP.  iTunes will not allow me to sync any of my purchases prior to August of last year and gives me a Not Authorized Error.  I completely repaved my 4s and still have the problem.  Similar errors when attempting to play on Apple TV (home sharing is enabled and works for all the content but this same group of purchased songs).  I did the basics of authorizing and deauthorizing, yada yada.
Here is a screen shot that I get while syncing.
Called Apple support and they gave me the run around saying I'd used two differnt Apple ID's. The MBP has a different Apple ID but iTunes and my iPhone are all under the same ID, the same ID I have used for all my purchases. 
Details.
MBP running OS X 10.8.2
iTunes 11.
iPhone 4s running 6.1.2.
Apple TV

Hi weotch2,
If you are looking to set up syncing on your new Mac, you may find the following article helpful:
iOS: Syncing your data with iTunes
http://support.apple.com/kb/ht1386
Regards,
- Brenden

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