New Nano - Can't transfer iTunes

I bought a Nano for my daughter for Christmas to replace an older iPod. I tried to transfer (by selecting and dragging) the music that we have on our iTunes into her Nano, but 2 things have happened - 1) the first time I tried it showed that they were being transferred, but when we disconnected the Nano the songs didn't show up. 2) I then synced the Nano to our iTunes and the songs show up but they are grayed out and won't play. The music is a mix of songs from CDs and from the iTunes Store. I tried to reset/restore the Nano since it is brand new, but I received an error message that it couldn't be restored. When I started iTunes back up the Nano appears to be fine with the exception of experiencing the same problems as before. What am I doing wrong?

I'm having the same issue.
I hooked up a new iPod. iTunes recognized it no problem. I dragged over a couple of songs. iTunes indicates that it is transferring the songs. I eject the iPod when it is finished. iPod indicates there are no songs on it.
I was previously using an older iPod nano. It worked fine.
BTW...using Asus laptop w/ Windows 7 64-bit and iTunes 9.0.2.25.
Thanks.

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