Automator Calendar and Events Dissapears after OS X Update
My solution to this was to abandon the Automaton Calendar in macOS and instead opt for using launchd.  My other option was cron but that has since been deprecated in OS X


  Darwin note: Although cron(8) and crontab(5) are officially supported
  under Darwin, their functionality has been absorbed into launchd(8),
  which provides a more flexible way of automatically executing
  commands. See launchctl(1) for more information.”


I have created and backed up all of the .plists that I need running on my machine and created a bash script that installs all of them in case I need to do a clean install of macOS in the future.

Full documentation on lauchd can be found on Apple's Developer Website