I disagree. The taxi driver (an analog to Charon the ferryman) specifically tells Jess that nothing can be done about the boy, he is dead and can not be helped…He is telling her that she can not undo these circumstances, though she will continue to try to no avail. I think the OP is correct, Jess is cheating him, as Sisyphus did, and is being punished and tormented for it, to break the loop she must right her wrong to the ferryman…though what her fate is after escaping the loop may potentially be worse.
Cast In The Name Of God…Ye Not Guilty

Kinda like Ground Hogs Day. She must make things right with the person she hurt the most.
So many stories, so little time.