IPod Video = no longer recognizes/updates purchased videos

I purchased a video from iTunes a while back and have since enjoyed it no my iPod. However, when I plugged my iPod in to update it last night, ALL of my videos/movies no longer appeared on my iPod. Sooooo, I updated it again this morning, and now it won't update a couple purchased videos. What gives?
I had to reset AND restore my iPod to even try to bring it all back. But still - no luck. SOME videos show up - but not a few others. Why is this?
What do I do now?

I forgot to specify that it is the Belkin TalkTunes STEREO device which is no longer recognized.

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