How do I get Itunes to allow music onto 2nd Ipod?

I've got 2 Ipods (one for me, one for wife).  When I plug my wife's Ipod into computer, Itunes recognizes it, but won't allow it to copy over some albums that were purchased back when DRM was the norm.  Is it not possible to share an older bought album?  I get this error message below....
"Some of the items in the Itunes library, including X, were not copied to the Ipod '(name)'s Ipod' because you are not authorized for them on this computer."
But the problem isn't the authorization of my computer, it already is authorized.  Is there a way I can get Itunes to recognize this second Ipod and get this albums copied to the second Ipod?  The home sharing information hasn't been helpful since it doesn't apply to just one computer. 
thanks in advance

You need to authorize your computer.
It has nothing to do with the ipod.  You can sync as many of your  ipods/iphones/ipads as you like.
iTunes repeatedly prompts to authorize computer to play iTunes Store purchases

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