Out of interest, what was your intended route?
My advice is "Always work out how you would fly the trip yourself!". Particularly with 'experienced' PPL holders! There is a fine divide between 'experienced' and 'complacent'.....
Even sticking religiously to the WW arrival procedure can often be difficult, thanks to the antics of some of the locals! And be especially careful of altimeter settings in that part of the world! I once asked Benson for the London QNH whilst transiting the Benson MATZ with a student practising UK airspace familiarisation and was haughtily told "Remain on the Benson QFE!". To which I replied "As I fully intend. Request FIS - now, what is the London QNH?"
Sorry that the CAA took you to court, but I guess 10 min of LHR delays is a bit different to sticking a wing into the Stansted zone or similar - so they probably had to make a point?