Personally I am not a fan of flight trivia Q and A for these sort of exercises. For an individual like this I think you should approach it as a practical " use your aircraft" exercise. The day before the flight assign a particularly demanding routing including as many different flight planing scenarios as possible including for example
-routings through high density airspace/hilly terrain
-flight over water
-destination near max range
-an intermediate stop at a short grass runway with no fuel
-assign a honking winds aloft and crappy but doable ceiling and vis.
When you go over the plan explore go/no go criteria for each leg and any areas where he has questions.
When you do the flight start the route and insert a few emergencies. When both of you are satisfied break off and do some upper airwork including for example manoevering at minumum airspeed ( i.e. see how slow you can go while doing gentle coordinated turns. Hint, if the stall warner is not on continuously you are not going slow enough) Take a hood and without warning while in a climbing or descending turn slap the hood down and say you just entered cloud. Practice any other manoevers the student would like to sharpen up. Conduct a full PFL and then recover to 1000 ft AGL (or the minimum safe/legal altitude and simulate a sick engine by reducing the RPM to the minimum required to just maintain level flight and return to the airport for a couple of circuits with different configurations
BTW the flying Club where I used to work had a policy that all renter pilots had to do an annual proficency check flight. I always included a PFL and
never had a PPL complete this exercise to a satisfactory standard and many were so bad I could only conclude that an actual engine failure would be probably result in a fatal accident. The reality is all pilots will be good at the stuff they do the most and less good at the manoevers that are seldom if ever practiced. Therefore I think it is important that this kind of exercise also be also used to review the less commonly practiced exercises.