This is more profound than it might seem. The big reason people don't play tricks like this is just social. It's embarrassing to be pushy, it's shameful to cheat, it's also meta-embarrassing to be caught spending this kind of effort on something as dumb as a train ticket.

LLMs can be prompted for shame, I guess. But prompts only go so far and to them The Task is always going to be paramount. Human riders have a life after the refund. It's not clear to me how one simulates that.