LOL great thread....
Some of my winners...
When staying at HPN, the area around the airport got too expensive, so management moved us out to Conn. They put us up in a no-name hotel that was slowly being converted into an old-folks home. Sometimes you got to share the floors with them.
Anyway, around dinner time, you would walk down to the lobby, and it was packed with the crochiest, meanest, rudest, ancient old New Yorkers that you could imagine.
You figured on seeing the ambulance at least once per stay.
Some people got the alzheimers floor. You had to call to get let off the floor

.
EYW and HHH: They tie as the places where the hotels have the mold growing up the walls to the highest level.
And WTF is with the showerheads? I HATE it when all you want is a nice shower, and all you get is a dribble of lukewarm water.
The Westin at ORD, OTOH, is very nice, EXCEPT, no discounts on food, and NO VENDING MACHINES. Crack that bottle of water in the room, and its regular price, 4 bucks, 4 bucks. Room service was spendy, so I went down to the sports bar to get something to take back to my room. The dude at the bar tells me I can't get anything to go. "OK", I say, "how about I take a bite, then get a box to take the leftovers"..."Ahhh mister, we would have to charge you the room service price then". I dined at the Golden Arches next door.
Of course, whenever there is edible food to be had in proximity to the hotel, it usually means crossing 8-10 lanes of Deathrace 2000.
Best,
Nu