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I am writing about a dozen different offices headed by locally elected sheriffs. There are other 'offices' in the story, so at least a couple of times I'll have to use the full phrase. In your view, is it better to leave the singular sheriff's and the plural offices? Or make both parts plural: sheriffs' offices?

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If there is more than one sheriff then it would be sheriffs' offices. It all depends on the number of sheriffs.

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