Of course, you can use testing, but then most people who will be subjected to a difficult test while playing the first version of the map will experience pain in various places.
You can set the priority of visiting locations relative to the difficulty. The lower the difficulty, the later the priority is given.
Added 3 minutes later
Does the bot somehow react to QuestionBoxForPlayers if it was sent to it? Or is there an exception when calling it on the bot? If the game presses "Ok" for it, that would be a good help. There must be a way to resolve this problem; the bot won't just stop because of a message.
I just checked the operation of QuestionBoxForPlayers. It seems that it is simply ignored by the AI player. And the functions that are activated when the "OK" or "Cancel" buttons are pressed are simply not executed.