So easily preventable(early spoiler)....
Wow, all Ben Affleck's character had to do was say 'Hey, I'm late for court and could end up without a job if I don't get there now. I can drop you at the courthouse and you can get a tow or you can wait and when I'm done, we can finish up.'. Done. They could have done all the insurance stuff while driving into town, and Samuel L Jackson would have made his court appt as well. If I had been in a similar situation, I most likely would have done just that. I definitely wouldn't have said 'Better luck next time.'.
Of course it would have been a 7 minute movie, but it would have gotten across the idea of 'Don't be a dick.', which is a motto way too many people don't 'get' now days.