idk if anyone tried this or if this is ur problem
But i ripped a youtube video and put it in a playlist in itunes but it didnt show up in between the songs, or in the video app on my ipad when i synced. i went back to my computer and told it to sync it under the movies tab, and still nothing, and finally after an hour of forums i went back to the movies tab and scrolled down and it says "Include videos from (Insert dropdown here). i selected the playlist and now the video works and flows fine i the playlist.
Note: I have an iPad 2 and this post is old so idk if it help so ya...