This is what I have so far, and it is a total mess. Mainly because I really don't want to use either TODAY or NOW but I can't come up with something else. I'm mostly a formula newb - I can do basic stuff and figure out what I have done wrong. This is what I have so far:
=IFS(OR(AND(ISDATE(O100),(EDATE(NOW(),-12<=S100), (EDATE(NOW(),-12<=P100)), (EDATE(NOW(),-12<=Q100)), (EDATE(NOW(),-12<=R100))))), "True", "False")
=IFS(OR(AND(ISDATE(O100),(EDATE(NOW(),-12<=S100), (EDATE(NOW(),-12<=P100)), (EDATE(NOW(),-12<=Q100)), (EDATE(NOW(),-12<=R100))))), "True", "False")