@Jeff Long this seems like a frequently ask question so I did a prototype but just hop onto a new project that also has to do with checklists.
One of the observation, and @Iain Dooley can correct me, is that for one to have due dates on checklist items and assignment, you have to be on business class board.
Once you have have that and you create cards out of the checklist items, and making sure they are in sync, then a Calendar Power Up should work against the target board. There are also other considerations when checklist are deleted, task gets unassigned, task gets deleted...because you want to keep the board clean. Fortunately, Trello has the mechanisms to connect these together but it can get quite complex.
incorporated the assignment and due dates just after I cut this video
Trying to come up with a simpler implementation.
Hello Community! My name is Brittany Joiner and I am a Trello enthusiast and Atlassian Community Leader. I'll be sharing with you a series of videos with my top tips on how to best use Trello...
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