What an excellent thread this has been. Very enjoyable and thought provoking. It's waht I like about pprune and long may it continue.
Coming to it late in life (ditto flying), I can understand how a professional person can bring their "baggage" into a new realm and suspect the pilot in this case may well have done. Competency in one field sadly isn't always transferable to another.
Being a trainer, I suspect the person involved may well not have taken on board "the music in the words". Instructors may well have multiple agendas. I'm (paid) to give the course - I got good feedback - hence that's it. In an ideal world it's "when this person leaves the course, I am satisfied that they can cope without me" (a perennial problem where I work - the management believe they are paid on delivery whereas you actually get paid on acceptance of the product by the client). I suspect also that judgment by the person involved in particular circumstances may be lacking. Was there sufficient understanding by them of the principle of the "superior pilot"?
Running out of fuel (viewed from the ground) is poor planning (assuming that the fuel system hasn't sprung a leak). Discovering it in the air is different and shows us a great deal about people's judgment and motivations.
Lastly, let's address the challenge of getting someone who's been in a crash back flying again.
From conversations with insurance principals, my view would be to get the insurance people to state their conditions for issue of insurance (e.g spend 25 hours flying with an instructor, do 6 diversions, plan 10 cross country flights etc.).
Basically, instill some practice to turn someone who has a bit of paper declaring their competence into someone who has met the subtle challenges that flying throws up over at least one season.
My own log book (spread over 25+ years) has many learning examples in its bland entries.