Music Won't Sync, "Computer Not Authroized"

I bought an iPod Classic 7th Gen 160 GB, but when I tried to sync my iTunes library with it, many songs (approximately 100 of them--some ripped, some purchased through iTunes/Amazon) wouldn't sync. The error message I got said the computer is not authorized to play the song, but when I try to authorize it and enter my Apple ID and password, iTunes says the computer is already authorized. When I go to the iTunes Store, it shows some songs have been purchased and it won't let me purchase them again. Help!

Yeah, not sure where the "Need iPod for idiots" heading came from, but I don't need that. This is my second iPod Classic. I had the first one for ten years, and I know how to use it. Just can't figure out why it won't sync.

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Place the iOS device in Recovery Mode and then connect to your computer and restore via iTunes. The iPod will be erased.
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RecBoot: Easy Way to Put iPhone into Recovery Mode
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iTunes impossible to sync - My itunes music won't sync. I have tried it all, resetting, deleting the library and reloading, turning on and off all the possible related buttons on iphone and itunes and still mosto of the music is still with a doted circle on the left that keeps the song grayed and although I hit SYNC nothing happens. Then, there are songs on the iPhone 6 that are not on the iTunes library. How can that be possible?

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I assume you are talking about iTunes on your computer, if so, you will have to remove all Apple programs associated with iTunes:
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Music Won't Sync, "Computer Not Authroized"

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