ITunes will not sync Store purchases

Right after my friend upgraded my iBook to Mac OS 10.4, I synced my third generation iPod nano with iTunes. After it spent 2 hours or so transferring the music (USB 1.1...), I get this message that says, "Some of the files including (whatever video it named) will not be synced with this iPod, because they cannot be played by this iPod.
What I don't get - I purchased these videos from the iTunes store. Shouldn't it download files in a format and size compatible with iPods?
All of them are in the .m4v format, and my iPod software is up to date, I have version 1.1.
When I right-click any purchased video in the library, there is no option to convert it for iPod/iPhone like there would be for any other. There is only an option Convert Selection to AAC.
I put copies of the exact same videos onto my iPod from my PC, and had no problems.
There are no settings in iTunes preferences that could have anything to do with this, so I am out of ideas.

The solution you gave me worked the first time, but when my iPod was almost done syncing, I realized it was still formatted for Windows, so I stopped the sync and Restored my iPod. Now that it is formatted for a Mac, I get the same problem. It says my iPod cannot play the videos, so it will not sync them.
I tried deauthorizing my computer again (about five times), yet the problem still persists.

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http://support.apple.com/kb/ht1351
Thank you for contributing to Apple Support Communities.
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ITunes will not sync Store purchases

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