Help wanted understanding checklists and automated notifications. Is there a better solution?

We have rolling admissions with no specific due dates. We had hoped to set up checklists so that when an admission staff member checked a box for a step on a checklist it would send an automated notification to that SPECIFIC candidate (not everyone currently on that step) with a message we pre-set. Now that we are into the nuts and bolts of it, we don't see any way to use the checklist and their notifications because we don't have due dates. How do other Blackbaud schools send automated notifications throughout their admission process?

I saw an older discussion thread that is related to my questions, but I wanted to open up my discussion to how rolling admission schools send automated notifications.