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Hmm, I'm a grammar pedant and that one has never bothered me except in formal prose (real journalism, marketing copy, books).

It's spoken that way ("one-hundred dollars") so it's actually kind of intuitive to write it that way, even if it's technically 'wrong.'

Oh really? Then why don't we say QUESTION MARK or PERIOD verbally for each sentence of you think the $ literally means "dollars?"

because we have other clues for that. A question is denoted by a raise in tone at the end of the sentence. A period is denoted by a pause.