I can sort of see what you're getting at here, but to me needing to ask "what question was being asked?" in order to do a correct analysis is really a special case of the need to condition on all information. When we know "the older child in that family is a boy", we shouldn't condition on just that fact when we actually know more, such as "I asked a neighbour whether the older child is a boy or girl, and they said 'a boy'", or "I encountered a boy in the family and asked if they were the older one, and they said 'yes'". Both these more detailed descriptions of what happened imply (assuming truthfulness) that the older child is a boy, but they contain more information than that statement alone, so it is necessary to condition on that information too.

For Technicolor Beauty, the statement (from Beauty's perspective) "I woke up and saw a blue piece of paper" is not the complete description. She actually knows sometime like "I woke up, felt a bit hungry, with an itch in my toe, opened my eyes, and saw a fly crawling down the wall over a blue piece of paper, which fluttered at bit because the air conditioning was running, and I remembered that the air duct is above that place, though I can't see it behind the light fixture that I can see there, etc.". I argue that she should then condition on the fact that somebody has those perceptions and memories, which can be seen as a third-person perspective fact, though in ordinary life (not strange thought experiments involving AIs, or vast cosmological theories) this is equivalent to a first-person perspective fact. So one doesn't get different answers from different perspectives, and one needn't somehow justify disagreeing with a friend's beliefs, despite having identical information.