And that would make sense the hotel would have a problem with it as well. I'm sure if someone tried that at the SF Union Square Hilton they would have an issue with it and if I was a guest on that floor I would have a concern.

I think it was a nice gesture but too risky for them as well. I would never want a stranger staying in a room that was booked in my name and credit card regardless of if they were homeless or claimed to be the CEO of a fortune 500 company. If they cleaned the mini bar out, order expensive room service items charged to the room, make international calls billed to the room or trashed the room you'd be looking at an expensive credit card bill and if they decided to have a party or do illegal activities in the room you'd risk being banned from the property.

I also thought Hilton (and all other chain loyalty programs) T&C said the actual guest had to be staying in the room it was registered to. There's been a few times people that I know very well will ask me to book the room so that they can get the lounge access, premium wifi, upgrades, etc. and I can get the points and stay credit and I'll refuse fearing I'll have my account closed (plus it isn't fair to diamonds staying in the hotel if they lose an upgrade to that guest or have to deal with lounge crowding due to someone that shouldn't even be there).