Something like a polling action? Maybe just apply it as a client setting?
setting "MyHealthCheck"="{now}" on "{now}" for client
Comparing times in Web Reports is a little tricky, but if it’s able to keep reporting in this state you could make it an Analysis Property:
MyHealthCheck Expired:
exists setting "MyHealthCheck" whose (now - value of it as time > 1 * day) of client
Should return “True” if the value hasn’t updated within the last day. You’d need to schedule this Task Action to “Repeat while relevant, waiting X hours between reapplications” and make it reapply more frequently than once per day.
You’d want the filters on a Web Report to catch computers with “Last Report Time” more than a day old OR “MyHealthCheckExpired” gives ‘True’