Question: How did the emergency operator start the car when Matt tells them to start? And why did Matt do so when McClane was ready to start the car with just the wires?
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Chosen answer: The on-board assistance system that Matt was using to contact the operator is specifically designed to allow for emergency usage in just such a way. They usually require a password to verify the user, which is exactly what Matt was trying to BS his way around. However, even though McClane is willing to hotwire the car, there are two problems with this. First, cars in recent years have become much harder to hotwire. Second, even if McClane was able to do it, the on-board assistance would have been triggered and it would assume (rightly so) that the car was being stolen and authorities would be alerted. With a likely GPS in the system, it'd be hard to get away from that one. By using and fooling the system, they now have the ability to get around unencumbered.
Garlonuss ★
Also, the airbags wouldn't have deployed when he hit the bumper with a trash can. They're designed to go off only when the vehicle is in motion thanks to a vehicle speed sensor that arms the system over a certain speed to avoid costly repairs in the event you just bump something or vandals just wanna be vandals. I remember a funny commercial with an elderly woman using her purse to hit a car bumper when the driver honked at her as she slowly crossed the street. Hilarious, but not accurate.