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It seems that sort by due date is for the "card" due date only. Is there a way to sort cards based on the due date of items on the checklist?
This is not a feature, though I wish it was. Please can you contact Trello and request it. Likelihood of it being implemented is low but worth a try.
Select, "Using Trello > Feature requests"
As a sidenote, I think this could possibly done via the Trello API, I will look into it and if I have any success I will come back to you...