Hi Charles,
when a Runbook Server is restarted, the Runbooks which were excecuting are automatically started from the first Activity.
When a Runbook Server has frequent errors to reach Orchestrator Database it stops and no Runbook will run on this Runbook Server until Orchestrator Runbook Services is re-started. So it's not possible to have a Runbook which monitors Orchestrator itself completely.
You need a external System to monitor, e.g. SC Operation Manager (SCOM): https://systemcenter.wiki/?GetCategory=Orchestrator+Runbook+Management+Pack
Regards,
Stefan