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I think I might have an insight into why this mission locks up the console when Hillary is destroyed by a tank.
I was recently racing Hillary with a six star wanted level (my current obsession) when he got rammed by the police Cheetah and went over a bridge into the water. My car got destroyed. I ran over to the edge and looked, and there was Hillary perfectly intact in his red car with the bouncing pink arrow. I ran down the street to grab another car... and suddenly Hillary zooms right by!
Now, I've seen this sort of "magic hand of the game developer" reach in and change the mission to keep things moving. In San Andreas, CJ has to off the cop with the Polish name and there's a chase through the desert area. Once he went off a cliff into the water, and then suddenly "magically" reappeared on the road.
But when Hillary is destroyed by a tank, all that's left is the bouncing pink arrow over his burned out car. No magic hand can do anything for him now.
There's a missing check in the program for Hillary's death in this case. You can finish the race to the end, but when you pass through the red marker by the Malibu, the screen goes black and locks up. But you can shoot Hillary in his car, and the mission correctly fails with "Hillary is dead!"
Since Hillary's car is nominally indestructable, the thought of checking for its destruction was never built into the mission by the game designers. So Hillary can be killed by a tank, you finish the mission... but at the mission's end, the game has to resolve the program loop and something's wrong: Hillary's dead. I wonder why it won't return to the main loop though.