I had whatever version was around when the video ipods came around (and a bodgy bit of hardware that was). I couldn't sort videos the way I wanted to - itunes says that that file extension means "tv episode" instead of "movie"? Sorry, it's a tv episode. Not to mention the terrible UI with tiny targets that doesn't blend in with the user's desktop theming. Maybe that was v4+, but all I remember is hating to use itunes (including managing updates as already mentioned)