Late check-out is my biggest source of frustration with all hotel properties and across all chains. Most places make me haggle with them in some fashion like this:

me: "I'd like a 4 p.m. checkout, please."
them: "Our checkout time is 12:00, but you can have until 1:00."
me: "Even for Platinums?"
them: "I suppose we can do 2:00. We're very busy." [Total b.s. in most cases, as I ask other hotel clerks what the capacity is.]
me: "I work at night and sleep in the day. I don't expect to get to bed until 9 or 10 a.m. You can't let me get at least 6 hours of sleep?"
them: "ugggghhhh....okay, you can check out at 4 p.m."

After all this crap, I end up getting awakened at 12:15 by housekeeping who was never informed that I had a late check-out, then again at 1:00 by security or a manager who is also unaware. So much for a good night's sleep.