Another local case is interesting regarding insurance company logic. A guy has CMEL-IR, 500TT with about 380 in a Baron. A couple years ago he was flying a leased A-36 Bo when a cylinder departed the engine and he deadsticked it into a field. Some damage to the airframe, but he walked away and the airplane was repaired. We all thought he did a hell of a job getting it on the ground so it could be flown again.
He decided to buy a 414, so we started shopping for insurance. The companies wanted a full 50 hours of dual & initial sim, same as for a guy with a new MEL. Turns out the insurance company didn't care how good a job he did handling the Bo emergency, or that it was a mechanical failure totally independent of his piloting skills. All they cared about was that he had some damage history on his insurance application, for which they docked him regarding his new policy.