Hello, just got a refurbished Macbook as the backlight on 1st gen. Pro went out.  Transferred everything but it does not want to let me connect the ipod.  I get this message

This computer is no longer authorized to play purchased items that are on the iPod “John Rowe’s iPod touch 2”. Would you like to authorize this computer for items purchased from the iTunes Store?  When I click authorize it gives me a very old email sign in.
  I change it to the current with password and then I get this message.
This computer is already authorized.
Including this one, you have authorized 4 computers out of your available 5.
And this goes around in a circle.
Any advice?
Thanks,
John

Did you try the suggestions mentioned here? iTunes repeatedly prompts to authorize computer to play iTunes Store purchases and About iTunes Store authorization and deauthorization

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