Long ago, a late arrival on a busy night at the Chi Palmer House Hilton, a very nice, but muchly harassed Honors Check In Desk clerk, apologized profusely, before sending me up to a 1BR suite "involuntary upgrade". I opened the parlor door to find a poker game in progress, more to the players' chagrin than mine....
Back downstairs, rollaboard and briefcase in tow, I was met by great apologies, and a proposal to bump me up the street (with no offer to pay for the night at the substitute caravansarai. I was in a "No Huey, Jose!" mood, and ended up, after summoning the MOD (More apologies!), in a lavish 2BR suite, all alone, except for a fruit bowl.
Pre-occupied rooms? Not as infrequent as you would think in this era of computers. Three times I can recall.