Errors with new computer

My friend just purchased a macpro in addition to his powerbook. Everything was brough over from his old computer. He is also signed into the music store. The message appears that"some of the audible files in the itunes library were not copied to teh ipod because you are not authorized to play them on this computer." I have checked some of the files and they play. Any help is appreciated.
pt
Imac g4, 12 powerbook 1ghz   Mac OS X (10.3)  

Yty to reauthorize the computer. See if this happens again after your friend authorize it again.

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    http://discussions.apple.com/thread.jspa?messageID=2831962#2831962
    What should I do with my iPod? Send it or keep it?
    http://discussions.apple.com/thread.jspa?threadID=469080&tstart=0
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    Sad Face on iPod for no apparent reason
    http://discussions.apple.com/thread.jspa?threadID=336342&start=0&tstart=0
    Meeting the Sad iPod icon
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    Sad faced iPod, but my computer won’t recognize it?
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    iPod Photo: unhappy icon + warranty question
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    4th Gen iPod Users - are we all having the same problem?
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    Sad faced iPod, but my computer won’t recognize it
    http://discussions.apple.com/thread.jspa?messageID=2242018#2242018
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    iPod making clicking noise and is frozen
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    I am not suggesting that you should follow as well, but just read them as your reference. You are the person to make the call.
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  • How do I sync my iPhone 5 with new computer?

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