So, take movies. For my N800, I start with a DVD and run it serially through two apps on my PC and transfer it via a file manager by SSH or a USB connection. I don’t see him wanting to do that. He, instead, opens iTunes, clicks a couple times, and then plugs in his iPod, which automatically synchs.
Admittedly, this survey of the “ecosystem” is heavily entertainment-oriented.*
Nokia, and every other company that isn’t Apple, really has its work cut out for them