Can see files in iPod folders on computer, but not in iPod

Hello - first time iPodder here . . .
I've purchased several songs from iTunes prior to owning an iPod. Since my purchase, I was able to move about 40 songs from my home computer to the iPod. All the remaining 100 or so wouldn't transfer for some reason.
As well, I use iTunes on my work laptop. I downloaded one movie & one TV show in from the iStore. I have a 30GB video iPod. It is set to manually move files (drag & drop). When I drag from my iTunes folders into my iPod, it appears to transfer correctly. I see the status window moving along slowly until the transfer is complete. Afterwards, I can see the file(s) listed in the appropriate folder under in my iPod section. However, after I eject the iPod, the files are nowhere to be found.
Am I doing something wrong?
Thanks for your help!!

Sorry - when I say they're nowhere to be found . . . I mean on the iPod. They still show up in the Library folders . . . and the strange thing is - they still show up in the iPod folders too unless I delete them.

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Can see files in iPod folders on computer, but not in iPod

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