Having trouble moving iTunes collection from old computer to new

I just made the switch from PC to Mac, and with the Macbook I got a new iPod (5th gen Classic 160GB). On my old PC I'm not having trouble syncing my new iPod with iTunes and getting all 1200+ files onto the iPod. The trouble starts when I try to sync my iPod with iTunes on my new Macbook; it says there are 26 files that can't be transferred to iTunes from the iPod because this computer isn't authorized, but I authorized this computer and it continues to say the same thing. Also, even with those 26 files not making it over, somehow only 257 of the 1200+ files on the iPod are making it to iTunes.
tl;dr Most of the files on my new iPod aren't transferring to iTunes on my new Macbook. CAN SOMEONE PLEASE HELP??

I haven't, I've been using the same account since I first got an iPod. Although...I just noticed that all the songs that did transfer are songs I bought from iTunes. None of the songs I imported from CDs got transferred. What's the deal?

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    The article at the link below describes a few methods and provides some detailed instructions on how to transfer your iTunes library to your new computer:
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    http://www.mydigitallife.info/2007/05/25/how-to-take-ownership-and-grant-permiss ions-in-windows-vista/

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    !http://signatures.mylivesignature.com/54486/122/A57996D55BE7ABB4A67DE686D381A27 4.png!

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