I genuinely don't know what will happen in Hall H or at NerdHQ, but neither does TH. And that's where my schadenfreude comes in. Sure Luke will have given him some best case scenarios. He may have even given him some worst case ones. And Luke may have placed very strict 'don't mention the TS' restrictions on both of those events. But at the end of the day, TH can't account for the actions of unknown human beings or every human being...and that must be killing him.
Both may run as smooth as silk but the anxiety he is experiencing now is the rod he made for his own back.