There's no practical difficulty with "I sold my iPod full of songs and deleted those songs from my computer." It's only DRM that makes the practical side of things difficult. (While it can be difficult to entirely delete all traces of digital files, no store has complained about the number of third-party servers that have "copies" of ebooks or mp3s between the originator and the buyer. The issue is accessible, going-to-be-used files, not mainly-inaccessible digital copies.)
It's difficult to *enforce* "...and I deleted those from my computer," but no more so than enforcing people not making photocopies of books before selling them.
If the argument is, "but the files are still available in your online bookshelf/store," then they need to *remain* available in that store.
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