Is it possible to add a field such that an end-user can add checkboxes as and when they need to? I.e. a little bit like Trello or Kanbanize works with checkboxes.
I'm aware of subtasks functionality - if that's the answer to this requirement, then at least I have confirmation of that.
You can not use checkboxes like that. You could create a label type custom field where users can enter and remove labels free form. This would be more lightweight than subtasks but also offer much less functionality.
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