We are looking to automate due dates on different items in a checklist. For example, when Checklist A gets added to a card with "confirm hours" as an item, set due date in 10 days. Or when "Confirm hours" item is marked complete from a checklist, set the due date for the next item in 5 days. Can this be done?
I am pretty sure at the moment item due dates cannot be automated.
That being said there is a work around if you are okay with using the card due date.
You can have a list of rules that change the due date of the card depending on what happens in the checklist. So for your example:
when an item starting with "Confirm Hours" is added to a checklist, set due date in 10 days
when the "Confirm Hours" item is checked, move the due date by 5 days
This due date will appear in the card not the item but if you don't have an overarching due date for the whole card then it will work fine.