Definitely plausible. They know that he crosses the road at certain times. So they park a car nearby. As he's approaching the road, the car driver is notified and tries to hit him.

Or - they can simply kill him in other way and report that he was hit by car.

Why would you need to drive around the block over and over? Cars can be parked.

I'm guessing this is if you need to pull off the hit in NYC or San Francisco.

It's pretty easy to track a person without being detected, it's probably a little harder than deer hunting, but it's not impossible.

Not knowing much about it, I would assume that tracking people would be easier so long as you're in civilization. A deer would be suspicious at the site of any human at all. A human only becomes suspicious if they notice the same human more than once.