I've gotten later check out several times at various deluxe resorts, once at a moderate and never at a value. It helps if you you are moving to another WDW resort, they'll work with you a bit more then.
It also depends on how many check outs/check ins they are going to be having that day.
You will never get late check out at a DVC property.
I got a late check out (1:00) at All Star Sports last August. I requested it when I checked in, the CM told me to check with the front desk the next day to find out if they would be able to allow it.
The next a CM at guest services said it would be fine and noted it in the computer. I don't why the first CM couldn't approve it.
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