I agree with other posters, 98% of the time I need late checkout, there is no issue. Only had issue at one place at an Autograph in Virginia when they were fully booked for a wedding, so I don't really fault them for trying to push back.
Recent trips without issue
Courtyard Clearwater, FL
Courtyard Pueblo, CO (proactively offered)
Courtyard New York Manhattan/Central Park (proactively offered)
W Union Square, NYC
The Notary, Philadelphia