Songs Transferred from ITUNES to IPOD NANO don't appear in IPOD NANO

Help. I tried to do something simple: add songs to my ipod nano. Though the songs "appear" in the itunes gui when the ipod symbol is selected, I don't see these songs in my ipod when I eject it.
I have updated itunes (6.0.4.2) and ipod software (1.1.1), and have restored my ipod nano. So with a clean slate, problem still persists. Except now, since I restored my ipod, I have NO songs on it, so it is worthless until I resolve this problem.
I got this ipod nano at Christmas and was able to load it with songs (eventually) back in January. So I have a feeling that a software update is screwing me up.
It is as if the itunes doesn't properly transfer the songs into the ipod, even though it appears to do so in the itunes gui.
Thank you for your help.
Toshiba Laptop Pentium 4 3.2G   Windows XP  

MORE INFORMATION:
I tried various ways to transfer songs into the itunes ipod icon: from library, from playlist, even tried transferring playlist. In all situations, the transferred songs appear within the ipod icon as they should, but ipod doesn't show these songs when ejected. It's as if there is a missing "burn ipod" step or something.
I tried installing older itunes software, but it wouldn't let me because I had a new version. I didn't want to uninstall my current version for fear of wiping out my entire library.
I am not ready to take this step yet. I am hoping apple has a fairly simple solution.

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