Which rule of the above do you occasionally bend?
Sadly, I have broken all of those rules at one time or another : ( Mostly I bend the plenty of time rule.
I think the pilot of the MU-2 broke a couple of the rules. 1. He was flying at night ( I consider that one problem, like weather). 2. He may have been tired (I don't know how late he was flying). 3. He might not have been absolutely competent in the plane ( I am just guessing, of course). So if you add in one more problem, a fight with the wife, an electrical failure, etc. and you have a recipe for disaster.
Just like Kennedy - night, weather, time, pressure from passengers. Three or more problems and you will die.
I was once cleared through a MOA in western Utah and I became the "football." My instructions were to fly straight and level through the restricted area. I had fighter cover and bad guys trying to break through and get to me. Sadly I couldn't hear or talk to the pilots but it was kind of fun watching planes appear and disappear.
I know Chuck Yeager said it, but I have a big problem with that too, because it can easily be the first mistake that kills you.