Is there any way to allow for 3-state checklists?

It would be really nice if there was an option available to allow checklist items to be either yes/no or yes/no/not applicable (ideally on a list item basis - but it would be acceptable to be a setting for a whole checklist field too). 

We want to enforce that a checklist be filled in prior to allowing a transition - but we'd like to allow users to specify either a tick or a minus for each item.  The minus would be used to explicitly identify any checklist items that they feel are not applicable in their case.  For example, a design document may not always be required for an epic, but we want people to think about it and indicate explicitly if they choose not to do one.

Right now I'm faced with either having people check off items they didn't actually complete, or having separate custom fields for each checklist item.

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There should be a "Checkbox" custom field which could contain your choices above. Then in the workflow, put a "Validator" that this custom field should have a value before transition.

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