iTunes dropped its DRM requirements a long time ago. If you bought stuff during the DRM era, you can pay a few extra cents per song and convert it to DRM-free.
All Willis had to do was call up a Genius Bar, and he'd be set. He'll pay more for legal fees than he ever would in upgrade costs.
I'd say that as far as iTunes music goes, this is DOA.
That said, transferring of ownership and rights still remains for DRM'ed materials, email accounts, social networking accounts, user passwords, etc etc....
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