Nicely done. But I could never pull off something like that, pointing out Hilton app inventory to try to force their hands and such. I'm a total wimp.

Even for a simple request such as late check-out, in US I'm nervous to ask and in Jpn my wife has to ask.
Lot of this is on me, but I also blame Hilton. At Hyatt, I can ask without being nervous because they always act like 2pm checkout is a slam dunk. At Hilton, you never know how they're going to react when you request a late checkout.