The JFK Jr. crash is actually used as a case study in pilot training today. Spatial disorientation cannot be avoided, but the key to learning to fly on instruments is learning to recognize it. That comes mainly through experience, which Jr. lacked. https://en.wikipedia.org/wiki/Spatial_disorientation
As far as faking his own death, keep in mind there were navy divers, crew of at least two navy ships, the NOAA salvage vessel, the FAA, NTSB, Kennedy family members, medical examiners, clergy, among many others who were first hand witnesses to the tragedy having occurred.
Yes, he had a Cessna 182 prior to buying the Saratoga. But that's just about as suspicious as me owning a Ford before I got my Buick.
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