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.
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.