In this case, it's much more plausible that it was a genuine misunderstanding.
I'm obviously not a lawyer, I have no idea if that matters. But going by my gut feeling, I agree with the outcome of both cases.
IANAL either, but I thought it was that obvious errors are not usually upheld in these scenarios. (Where "obvious" is something like "a reasonable person would think…".) So a $1 car would probably be an obvious error, unless there was some reason for you to think the car was worth nothing. (A $1 car where you purposefully manipulated the bot into making that offer… well.)
But here, there seems to be nothing obviously wrong with the chatbot's offer. Bereavement flights/discounts are a thing, and permitting someone to file the necessary paperwork after the fact for 90d also sounds reasonable, since deaths can be sudden and unexpected, that would be a kind thing to offer.
The court's ruling seems sound here. "Our chatbot is a separate legal entity", OTOH…
I doubt that the dealership would feel their intent mattered if they overcharged the same guy and he balked. Isn't that the whole goal in this stupid way of buying cars that we have to deal with?