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People can volunteer to pay royalties on used books, but there should be no pressure to do so. Buying something gives you the right to sell it to someone else, unless there is a contract prohibiting that.
Incorrect. You didn't buy it in the first place if there is a contract. That's part of the meaning of "Sale".

One is a completed transaction, the other is a contractual relationship, and the ease of entering into one-sided contractual relationships on the software age has me thinking we need to take a hard look at contract law to figure out if we're using it in a way that is really helping society in the long run. If you go off the essential intent and spirit of contract law, you should have direct, trivial access to those you're trying to enter an agreement with to alter terms. You don't have that. No one does.