CANNOT TRANSFER SONGS TO IPOD

I purchased some tracks off the iTunes store, and while they appear and play perfectly well in my iTunes library, I can’t actually transfer them to my iPod. Or rather, I can move them there, but they won't play.
Any advice would be much appreciated.

I have the SAME problem. "Updates successful" message followed by missing songs on the iPod and next update attempting to transfer these songs all over again. Tried everything, including "strange iPod behavior" suggestions to no avail. This has started since the January installation of the new iPod Updater.
Please help.....
  Windows XP   20GB iPod

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