Would some kind of checklist work?

For each designated time (morning, lunch, ... ) do not pass GO until all items are checked.

I helped a med school instructor with zero budget, and fortunately enough, a bunch of iPads in the storage room.

For a patient assessment class, he needed a big checklist, so I set up some trivial code in Numbers (Free Excel) and that worked very well. It even collaborates these days, though we never got there, though a copy of the sheet on shared storage is fine.

or some automated/automator action.

One virtue is that all prescriptions can be embedded in the sheet, for the benefit of physicians with a copy of the sheet.

Missing piece? Without too much data-gathering, please note that grapefruit interferes with some meds. Nobody ever asked.

I use a button reminder for my daily pills and for my epileptic dog.

Been using it over the last three weeks and not one missed dose/double dose because it’s right next to the medicine cabinet, chirps at us when it’s time, and logs presses to Google Sheets.Both my partner and I have access to the chart so we can easily see when a dose was given by the other + the physical form of a button that site right next to the pills helps. We don’t always have our phones on us at home.