Do you think it has anything to with the type of file uploaded? I uploaded that robin williams video he's talking about. I first used a software (VideoGet) to download it from Youtube and convert it to .wmv. Then I uploaded the .wmv file.
I've also tried uploading a .flv but I find that most of the videos I uploaded can't be downloaded succesfully. Of the 11 or so videos I've uploaded I only have managed to get 2 on my zune.
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