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The dollar isn't missing.
In the end, the men didn't pay $30. They paid $27. Plus the $2 kept by the bellhop = $29.
The riddle tries to fuck you up by *adding* the bellhop's $2 rather than subtracting it as you should to get to the clerk's new room charge of $25.
3 men paid $9 each = $27
$27 - $2 kept by bellhop = $25.
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