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I'm not optimistic on this working for say an arena or stadium concert, only the club circuit. Event promotion has a lot more than just selling tickets and bringing in a band. You have to advertise the act to sell the premium seats. If the show does not go on, the advertising money is gone.
And it's difficult to get any kind of event liability insurance with a calendar date of "maybe" or an expected crowd of "it all depends."
Try running Monty Python's argument sketch against the chatbot. Playing as the in house arguer (not as the customer), it quickly turned into a relentless "Yes! No!" discussion.