My last stay at a residence inn I was offered 3pm ilo 4pm and 2,500 points at check in for my inconvenience, which I was happy with tbh, but also mentioned to call the afternoon of check out to see if they could be more flexible if I really needed it.

Called down around 2pm the day of check out to see if they would be ok with 3:30pm as I had a call 3-3:30 and ended up leaving at 4 anyway … all in all while it was a little work it was one of my easier denied late checkout conversations.