How did Cain know what hotel/motel she was staying at and how could he upgrade her room without permission from the person, her boyfriend according to her, who booked it? No hotel/motel would go along with that. According to her he didn’t even know why she was there until they were at the restaurant.
The only hotel that fits her description (two blocks from the White House) is the Willard House. Suites there range from $500 to $1,700 per night, plus taxes. Cain forked out that much cash for a woman who was with her boyfriend? Yeah, right.
Actually they would go along with it if Cain knew the management. It wasn’t far from the offices and it’s possible the NRA used the hotel.
I worked in 4-5 star hotels for 30 years. We got these request all the time and accomodated.