Trello doesn't natively associate due dates to a checklist item.
Trello was implemented with the Kanban/Scrum development methodology in mind.
The Scrum approach is that the functional value associated to the card needs to be delivered by a certain date (end of sprint, release date, etc.) the delivery team needs to be empowered with the ability to self-organize enough in order to ensure that checklist tasks are done in the right order and on time for the next task to start. Daily scrums serve to ensure that coordination happens on a daily basis to keep tasks moving ahead.
If a checklist task needs its own due date, you may have to break it out into a card and change the checklist item to a link to the card.
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