He's not paid to hit the $5,000 every time. He's paid to give the wheel a final spin, ask the next player in line for a letter, and if it's in the puzzle, give them three seconds to solve it. I imagine he's just instructed to reach down and give it a whip.
Also, no, I can't imagine the kind of muscle memory it would take to be able to do that. Basketball players don't hit every single free throw, either, and that's with a target that never changes from being 15 feet away and ten feet above the ground.