Well this is a supplmental essay and it seems to be specifically about experiences in health care. What is the actual prompt or is the topic his own? Is he applying for nursing or a health-related field?
I would think there might be a way to include both approaches. He could being with "In recent years I have had three experiences in health care: (list). One of the most engaging was…and then tell his story.
It does sound as if the prompt is asking for info on all experiences, so I understand where you are coming from.
However, ultimately, it is indeed his choice 
Many of us old-timers can tell you that in the long run, it is your relationship that matters, not the application or college.
One thing you can do is get a third person involved, to avoid arguments. Just for the essays, for instance.