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I don't think that's the simplest answer, though. Usually, when these kinds of riddles use double meanings like that, it goes out of its way to not give away which meaning of the word is being used. But here, it is clear that the riddle uses the word "letter" to mean a glyph: "the letter A costs two dubloons." If the riddle had said "the character A costs two dubloons," then maybe the word 'letter' would mean the whole sign.
I still think there is a trick, though. The phrase "Cap'n Threelegs commissioned the sign to be made" sounds most contorted, so I wonder if the trick is there.
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