ITunes Won't Sync T.V. Show to iPod Classic

All of my videos have been converted to a specifically Classic 5th-Gen compatible MP4 format, and I've had no problem at all with all of the HUNDREDS of others in my iTunes library. But for some reason, one particular show just simply will not sync to my iPod, and I'm at a loss as to why.
Once again: None of my videos were bought from the iTunes store, and the dimensions, container, decryption, and absolutely all details about the video formatting is identical to the many, many other videos which have worked flawlessly as they were all created in exactly the same way, so file parameters should not be the culprit here.
I have my library set to sync only checked videos (due to space limitations) and have checked and double checked and triple-checked that this particular TV show is indeed checked when the iPod is synced. I've tried deleting all of the videos from the iPod and then syncing JUST this show, to no avail; I've also tried deleting and resyncing ALL the shows. No matter what I seem to do, iTunes simply will not sync this show. I don't get an "iPod will not play this file" error message or any kind of error message at all, and the videos play perfectly fine in iTunes. When I sync, the episodes just don't sync--they don't appear in the iTunes header saying "Syncing video 1 of 13" or whatever the numbers may be, and the sync says it finishes immediately. I'm really at a loss here.
The iPod is (I'm pretty sure) a 5th Gen iPod Classic, and the show is the first season of Metalocalypse. Does anyone have any ideas what the problem might be?

I FOUND A SOLUTION. at least, I was having the same problem as yall, and I found a solution that worked for me, I hope it helps yall too.
My issue was that music would sync to my devices, but some of the playlists would not have all of the songs in them that they should have had. I looked at the playlists, that I was having issues with, and they were all complex smart playlists. Meaning they had multiple levels of conditions in the smart playlist settings, and itunes 10 does not seem to suppor that. To fix it, I went through all of those smart playlists and made new smart playlists that had the same (or as similar as I could get them) conditions to my old playlists. I then re-synced my devices and all my songs appeared in my playlists.
I dont know why, but itunes 10 no longer supports some of the smart playlist rules that older versions of itunes did, so hopefully updating your smart playlists will fix this problem.
Best of luck guys.
P.S. if you dont know what I mean by 'complex' smart playlist, here is an example of what I mean:

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