The loophole for the hotels so to say it the availability. They have to take into account cleaing staff, who needs to be available for late check out cleanings. There is also a need for people checking in ahead of the official check in time. Even if check in time is 15:00, the status members expects to be able to check in ahead of time. And If you have a house full of members who ask for a late check out as part of the benefit, this will not work, if check in time is 15:00. So there are rooms, but there are not available for late check out. Because the hotel otherwise could not guarentee a check in time of 15:00 which might result in bad reviews. The last thing a hotel wants to have.

It is not what one want to hear. But even with highest status I have experienced that 14:00 was not available. And it is the same with Hilton. It very much depends on the hotels, the time of the year and how fully booked the hotel is.

For example, with late departures from Asia to Erurope, I simply book a night more.