I'd say using iTunes requires less technical acumen than keeping a Windows installation running and virus-free. Re: expecting users to be digital archivists -

I'd say using iTunes requires less technical acumen than keeping a Windows installation running and virus-free. Re: expecting users to be digital archivists - you may as well ask why anyone not a museum curator buys antiques, or anyone not an archival librarian keep books. Users may not expect their digital collection to last any longer than their collection of 8-tracks.