ITunes won't load all my songs onto my iPod Nano since update.

Ugh. Before the update I had no issues updating my iPod and now it won't update all my songs because it says my machine is not authorized to play them? What does this mean? Some of these songs I purchased on iTunes and other were songs I have from my Cds? And it also says I have 4 other machines operating on iTunes? I am not sure how this happened? I have restored my iPod and I am still getting the same message. This is so frustrating! This is why I dread updating. Please help!
PowerMac G5   Mac OS X (10.4.4)  

yes.

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