He may have given up, or might be a mythological figure from the underworld.
It's possible that the driver assumed she was going to go up to the boat, talk to people, then come back. So far, we have no indication that she told him she was going on a cruise. Upon seeing her board the boat, or after waiting for a long time, he may have given up on it and left without his money. He could visit the harbor shop, or some other means to try and figure out who she was for money collection purposes.
Another theory is that she is trapped in an underworld. Note how they mention Sisyphus in detail aboard the cruise ship. Sisyphus was eternally punished in the underworld for his actions. It could be said that Jess was condemned by the gods for striking her son out of anger, killed in the car crash, and that the taxi driver is Hades (or more likely Charon, since he is ferrying her to her punishment). He also is surprisingly casual about removing a grief stricken mother from the car crash, and says he expects her to come back in a knowing manner. It seems like something is wrong with this guy.
Therefore, you would not have multiple copies since the driver either leaves in each iteration, or is an architect of the loops unconstrained by the repetition.