As to the pilot, his past is colorful for sure. Just the fact that he has changed his name numerous times is very unusual. Other than trying to hide from creditors, family, or business partners, I can't think of any good reason to keep changing names. I wonder how much time anyone will spend really digging into his past.
There is the mandatory exhaust pipe change out to keep the exhaust from burning through the spar. but the over speed sound was pretty telling. I like the pilot was in witness protection theory the most. Italian restaurant far away. There used to be this Italian restaurant in Omaha. The owners seemed very out of place.
If his credentials were genuine, and he and the airplane were current and legal for instrument flight, then why was there not IFR flight plan and no communication with controllers after he departed KFUL? He was clearly intending to fly into IMC that day.
I don't normally speculate about crashes, but nothing stops me from writing a fiction short story that is very loosely based on the speculation surrounding this crash.
In this fiction short story, the pilot character was in the Chicago mob all through his early life, rising from a street thug to a serious enforcer. He spent his hard-earned money on flying lessons, earning his multiengine and instrument ratings. The mob realized that his talents were being wasted on the streets, so they 'found' a 'misplaced' Chicago PD badge that he could use to infiltrate. He was able to work in the police department's airborne department, pretending to watch traffic but really being the mob's eyes in the sky.
But he decided to go straight, so he turned state's evidence. He disappeared into the witness protection service, and kept only the police badge and retirement papers that the head of Chicago PD's HR had been sworn to secrecy about as souvenirs of his life on the inside. Out in the cold, he tried his hand at running a restaurant, but unfortunately he didn't know what else to talk to his cop customers about other than his time in the Chicago PD. The mob, of course, got wind of the restaurant and tracked him down. But they got poetic with the hit.
The mob's electronics guy snuck into the airport and rewired the guy's radios to always transmit and broadcast on a frequency outside the usual band, like 138.53. They set up a ground station with a few wiseguys manning it so they could pretend to be different facilities to the guy. He called up for clearance and they gave him one. He called for taxi, takeoff, and departure, and every time got a different fake controller. And eventually, they managed to get him lost bad enough in the clouds with crazy vectors that he lost control and crashed. They knew they could get away with it, because the pilot's history of what appeared to all ATC facilities as his ignorance of the FARs would make everyone investigating the crash chalk it up to a reckless scofflaw's loss of control.
In the novel version of the story, the pilot is a secondary character. The protagonist is his long lost nephew, who was trying to repair the radios recovered from the crash site and discovered the mob's subterfuge, then began to seek vengeance on his uncle's many enemies.
That entirely fictional back story can explain why he was always in IMC without talking to ATC. It can explain why he kept changing his name. It can explain the unverifiable Chicago PD employment. It can explain everything.
Of course, "guy who makes up stories about his past and regularly flies VFR into IMC eventually runs out of luck" is an equally fitting explanation. I think that we ought to rule that explanation out before we go too far into the weeds on alternative theories.