Currently I'm using an Apple calendar event to open a file, and the file is nothing but a macro trigger file.
I don't believe Apple Reminders send any kind of detectable event.
Maybe one day Apple will let you specify a Shortcut, and that could trigger a macro.
Your solution seems pretty reasonable.
I believe that's quite impossible.
It's a miracle you can still launch a file using the Calendar – it hasn't been able to run AppleScripts for years now – unless you use applets (which I believe must be code-signed now).
Keyboard Maestro has periodic triggers, so you can use it to trigger timed events. It's not quite as simple as just entering a date and time, but it can be done and isn't too taxing once you learn how.
Unfortunately Keyboard Maestro cannot wake a Mac from sleep or from a powered-off state, but if you want to put in the skull sweat you can learn how to use the macOS Power Manager.
-Chris
Thanks for the prompt response.
And thanks for the input. I appreciate it.
Whoa that's some extravagant stuff to be learned.
I am from a non-technical background so might not make a sense for me to embark on that learning journey. Moreover, I use calendar because it enables me to see macros in calendar format (date wise).
Thanks for the prompt response and valuable input. I did not know such things exist.
P.S. : Cron trigger sounds interesting.