Good idea. Below is a sql script I use to identify servers (I use SMS) not checking in. Perhaps, you can use it as your intial dataset to trigger actions.
SELECT a.[Guid] ,
a.[Name] AS 'Computer Name' ,
a.[User] ,
a.[OS name] AS 'Operating System' ,
c.[LastConfig] AS 'Days Since Last Check In' ,
c.[LastConfigDate],
IsManaged
FROM vComputer a
LEFT JOIN ( SELECT ResourceGuid ,
LastConfig = MIN(DATEDIFF(dd, [StartTime],
GETDATE())) ,
LastConfigDate = MAX([StartTime])
FROM Evt_NS_Client_Config_Request
GROUP BY ResourceGuid
) AS c ON c.[ResourceGuid] = a.[Guid]
WHERE c.[LastConfig] > 0
ORDER BY c.[LastConfig] DESC