Hmm, sounds like this hinges upon getting all breakfast charges and resort fees removed in one fell-swoop by the first agent. If the rooms end up being on separate folios, does it rely on the goodwill of this first agent? (Is it simpler when both rooms are on the same folio?)

Also, I'm afraid I don't fully understand the importance of checking out the second room at a different time as the first room, and furthermore to have a separate agent do the second room's checkout.