Stupidity: Howard has the opportunity to shoot Jack at the end, but doesn't for no discernable reason; he's already committed multiple felonies, and shooting Jack would help cover his tracks all the better. In fact, he could even have just taken the cash onto the subway and left Annie behind while staying in full disguise as a cop.
Suggested correction: Howard Payne's taunting dialogue in the subway station suggests that he wants Jack to live a long life, tormented by the fact Payne was able to beat him. He doesn't become intent on murdering Jack until the dye pack goes off, ruining the money. After that, he tries to shoot Jack but runs out of bullets, then decides to beat him to death with the detonator but fails.
Stupidity: When seeing that the bridge is out, JLC could've easily climbed out of the sunroof and hop off the back of the limo and onto the pavement, suffering a few cuts and bruises at the most. I know that it would've been anticlimactic, but still.
Suggested correction: You're assuming that jumping off a runaway car is a simple task that anyone can do. She's scared out of her mind, and many people in a similar situation would probably be scared at the prospect of jumping off a moving car, even with the knowledge that they will be flying off the road shortly.