ITunes library will not move over to iPod!!!

Please help! I am trying to simply move my music from my library to my ipod and it won't work. Every time I try to drag the music over or import or move songs into a folder and then into my ipod, the "No" symbol (ie: NO smoking sign) comes up. Each of these songs in file form has a little lock logo on it, I guess the songs are protected. I'm not sure why my Ipod is not recognizing these songs as mine. I have a ton of purchased music that I cannot get on my ipod. It is so frustrating. Any help would be greatly appreciated! Thanks!

"Some of the songs in the iTunes music library, including the song, "__insert song name(s) here__ were not copied to the iPod because they could not be found."
As stated, this means iTunes cannot find the songs.
Look in iTunes at those songs. They're probably gonna have a yellow exclamtion point in front of them.
The other error;
iTunes displays a -69 error when syncing iPod

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