The problem is that you are not buying the book or the file: you are renting use of the book in a digital format for your lifetime. When you die, the license reverts back to the copyright holder. For this reason, if your file becomes corrupted, or you purchase a new ebooks reader, then you can re-download the book. But you do not have the right to sell or "will" your ebooks to anyone else. You don't actually own your ebooks. You have merely purchased a lifetime lease on a digital copy of the book. That's why there is no legal secondary market for ebooks.
If the laws had been written with consumer benefits in mind, then there would be legal secondary markets for ebooks. But the ease with which a file can be copied multiple times and the complexity a workaround would have required meant that the law was written to maximize protections of the copyright holder and the sellers.
The reason you can't sell your ebooks is simply because you don't own them.
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