Fomalhaut30: How do used record stores verify that you haven't made a copy of the CD you're selling? How do used book stores verify that you haven't photocopied the book you're getting rid of?
If that company is taking steps to deauthorize that song track on your iTunes account, that should be good enough. Iirc, they also do not allow music purchased from Amazon's MP3 store.
There is no such thing as de-authorization on iTunes for music anymore - iTunes has been DRM-free and hasn't required authorization for playing iTunes (or any music) for years. That's the problem. Please understand that I do not necessarily agree with the following (nor do I necessarily disagree), but I feel it is important to lay out, clearly and without bias the opposing argument. The argument for why this method is copyright infringement is as follows: to transfer a purely digital file, unlike with media tied to a physical thing, necessitates a copy first, then delete. The record company argues that the store does not have the right to make the initial copy even if they make or think they make a deletion afterwards. Current law would stipulate that the copy process is against copyright. Further they claim, that since the music is DRM-free the delete process isn't clean to ensure that the material was actually transferred and not just copied, but their strongest argument would appear to be that the initial copy process is what's violating copyright. The judge seems to indicate they have a case, but whether or not they will win on these grounds is unclear.
The difference with physical media, is that while you have to trust that someone hasn't deliberately copied a physical item before transferring, here once something has already been transferred - thus there are briefly multiple owners - you have to then ensure that you properly dispose of all copies from the original owner. Physical media thus requires active dishonesty for the transfer to be a copy, while DRM-free digital media requires active honesty or at least a great deal more trust that the transfer is indeed a transfer and not copying of ownership. Current laws cover the transfer of physical goods, but not the copy-delete transfer of DRM-free digital goods.
As you yourself pointed out however, let's say that iTunes music had to play through iTunes and it had to be authorized? E-books, movies, and audiobooks are still like this both in iTunes and practically every other major store that sells them. Then you have a point. The transfer is a true transfer without a real copy process - all that is required is that when one iTunes, or say Steam, account becomes authorized to play a movie or a game, etc ... the seller has simultaneously been de-authorized to play said item. The catch is if someone had deliberately cracked and then copied their now sold DRM'ed media, but as you say that's no different at all from someone deliberately copying the media off of their physical disk. In fact, doing so is actually harder with DRM'ed media than just simple physical media - perhaps not hard, but certainly hard
er. So really with account-based DRM purely digital material, there are just as many if not many more protections to ensure the transfer process was indeed a transfer as with physical media. Thus, to me it would seem obvious that systems with account-based DRM should also allow the transfer of that media. However, one should recognize that transferring ownership of DRM-free material is indeed trickier and not quite the same process as we currently have with physical media and thus may not be covered by current first-sale doctrine.
Unfortunately for ReDigi, iTunes music is DRM-free with no authorization required even within iTunes to play music bought on iTunes or elsewhere. They say they want to expand to e-books and movies and I think they should've started with those since for every major store including iTunes those are still under DRM and require account authorization. They would've had a much stronger position to argue that their transfer process was compliant with current first-sale doctrine.