In the Orlando situation you will only be able to get points from the room you actually occupy. You cannot combine folios when the two rooms are at different hotels.

In the second case you may be able to combine the rooms into one folio. You will only be able to get points for two rooms; the one you occupy and one other. You are not suppose to get points for more than two rooms. If you have your room as an award then you can combine it with a second room, pay for them under one folio (yes I know one room is an award).

The Diamond member staying at the hotel is the only room entitled to the benefits. The hotel may extend the benefits to another room, but maybe not. It is up to the hotel.

Be careful booking rooms under your name if you are not actually staying there. Some hotels may want to see you actually "check in" before giving any benefits including points.