Unless they knew he had something very valuable, this is a poor strategy
Nope. If you don’t want to get caught, best to keep going. Getting a few extra bucks on the victim’s person won’t compensate for the jail time (though...we are talking about NYC here). Or, as others have speculated, this may have been a targeted hit to retrieve something of value.
Agreed poor strategy. Likely to cause more damage to the car than they are going to find on the man.
But they might be sending a signal.