Can only sync up to about 8 gig (on a 30 gig)

I've been having this very frustrating problem for a few months now. I have a 5g 30gb iPod, and it works great in all respects but this. If I try to put more than about 8gb on it, manually or sync, it freezes, throws up an error in iTunes (Required File Cannot Be Found), and stops. After a few rounds of this, it then needs to be restored and works fine again until it hits the 8gb mark. Now, during day to day play, it works great. No skipping, freezing, sluggishness- nothing. I can avoid this problem by keeping myself under the 8gb mark, but then its like I have a really bulky nano. Frustrating.

I wonder if the bit rate is too high?
I just read the iPad tech specs, and they say "up to 2.5 Mbps".
Your video appears to be about 9.5 Mbps.
I've heard that Canon 5D Mark II videos don't play as well, and it could be for the same reason.
It seems we may be stuck with compressing the videos in order to play them. Sigh.
Apple has video technology in Quicktime Pro / Final Cut / etc. Why can't they just put some of it in iTunes. They should make it easy for any video that the desktop will play to be played on the iPod / iPad / iPhone.
I bought an AppleTV to play my home videos on my TV. I knew that its output format was only 720p, but I was shocked that there is no automated way of playing my 1080p home videos without manually compressing them.

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