You don't need conspiracy theories in this case. Computers and copyright law are fundamentally incompatible because copies are explicitly made in the use of digital media. Some situations can be dealt with through licensing since it is enforceable, such as downloading a file from the vendor's server onto disk or copying a file from disk into memory. These are enforceable because transaction records may be kept, may that be the vendor's server logs or the vendor's reading software. If a copy of the data doesn't have a transaction record that compiles with the license, it is likely in violation of the license.

Other cases cases are harder to deal with through licensing since they are difficult to enforce. A vendor may permit the resale or transfer of the media through their own servers because they are maintaining the transaction history. (Problem is that they don't want to do this because it is not in their interests.) An individual could do the same, but you run into the issue of verifying the authenticity of that transaction, either because the logs are easy to forge or no record is kept. In other words, it is not possible to verify whether a transferred copy is in compliance with copyright law.

ReDigi is an interesting case because they were handling that sort of thing. Yet it does raise the question: how do you determine who is permitted to transfer media? The simple answer is that you leave it up to the vendor or trade organization, which raises the problem where they don't want to do it because it is not in their interest. The other option is for the government to license bodies. That runs into a brick wall because people either don't care about such issues or because people are opposed to government sticking their fingers into things (and many of those people are the very same ones who want to see the resale of digital goods).

So we end up back where we started: you can't resell purely digital goods.