Right now, it isn't possible to set multiple due dates per card, for example on checklist items.
The closest workaround, which requires a bit of work, is to use cards as placeholders in checklist items. When you copy a card's URL and paste it into the checklist item, the URL becomes properly formatted and you can see the card title. That card can have a due date, members, additional checklist items, etc. Hope that helps.
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