Hello
I am sure i have read that this doesn't work, but when i plug a new playbook into my pc it asks me what media source am i using, WMP or ITunes. I selected itunes and then transferred some movies. The media shows a successful transfer but i cant find it on the play book.
If the content is DRM, it will not transfer. This probably limits the transfer to home movies and the like that may be stored in your iTunes library. I have only used it to transfer music.