Reminders at random? (Inspired by Nested Folders #82)

On the most recent episode of Nested Folders (82: All-Consuming Problems), @RosemaryOrchard mentioned using a shortcut that will select reminders at random and create a notification. Does anyone have suggestions for how this might be done?

Currently I use Due for this kind of thing, but I’d rather not continue to mix time-sensitive alerts with what I would categorize as helpful prompts (stuff like, “Should you drink some water?”, “Are you distracted right now?”, etc.).

Ideally I would use stopping my wakeup alarm as a trigger action—I’ve tried this with Due, but it creates a fairly rigid schedule since new reminders have to be scheduled x many minutes after the shortcut is run.

Anyways, just looking for thoughts and suggestions before I spend an afternoon going down this rabbit hole.

You could schedule a shortcut like this to run at specified times during the day using personal automations.