Authorization is screwed up

I have iTunes 11.1.4 on OSX 10.7.5 displayed on an iMac. I have some apps I want to transfer from my iMac to my iPad. When I start the sync process and it gets to step 3, I  get a message stating "The iPad could not be synced because this computer is no longer authorized for purchased items that are on this iPad." It then follows up with "To authorize this computer for items purchased from the iTunes Store, choose Store > Authorize This Computer...
I follow the instructions using my Apple ID (which I know works because I login to other stuff without and issues) and once entered and I've clicked "OK" I get another popup stating "This computer is already authorised. Including this one, you have authorised one computer out of your available 5." 
"Huh" it says this computer is already authorised?, so I try again to sync and guess what? I get the first message again stating this computer is not authorised! What the ****.
Please tell me this is an easy fix.

iTunes repeatedly prompts to authorize computer to play iTunes Store purchases. If you are in the US you can freely redownload a purchase, so if the link isn't helpful, then try deleting the apps in question and then try redownloading them.

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