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I was testing Trello premium to see if it's worthwhile having work pay for it for me. One of the features I really like about premium is the ability to assign individual checklist items to an individual.
I tested this however and there is no email notification sent out to notify the person when there is a due date on an individual checklist item. Ideally I would want that I can set both due dates on a task as a whole and also on a checklist item. There will be instances when an a task will not need a due date but the 3 checklist points within that task do and the individual they're assigned to need to be notified, otherwise (for our purposes) it renders the due date useless.
Have you checked our reporting tool? Blue Cat Reports is a 3rd party Trello power-up that can help you filter cards and then you can set up email notifications with the updated cards each day.
What might help you in particular is to set a filter for due date and member from a checklist report and schedule a daily email with this list. After you configure everything you want to see in each member's report, you can schedule to send them out to yourself or to relevant team members daily (weekly/monthly also available).
When you sign up for a trial with us at Blue Cat, you can reach out to our support through the app and we are happy to help with creating a list as the above or anything else you might need.