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Q. In the money examples in the hyphenation guide, I would not have allowed the last example, “a $50–$60 million loss.” Almost certainly “a $50 million to $60 million loss” was meant, but the construction reads “fifty dollars to sixty million dollars.”
A. Luckily, in most contexts misreading is unlikely in the way you suggest (“Yes, it was a bad year; I suffered a loss between fifty dollars and sixty million dollars”). In the rare instance where such an expression could cause confusion, a writer should expand the range.