I tend to be flexible, if possible, with check out times. I am way less flexible about check-in. For check outs if they ask, and I know that the room is either not rented that night or that my check ins are arriving on a later plane, I am happy to give them a bit more time. However, so far, when I have had to say no (and offer to keep their bags in the living room), they have been very pleasant about it. The one time I had to say no and could only offer the back porch as a luggage holding area, again, they were pleasant, but not wildly happy. However, this group arrived with only 3 small backpacks so I didn’t feel too horrible.
Check ins. I have done two past-my-bedtime checkins and they went well, but, and this is a big but, the communications I had with them before their arrival led me to believe that they would be responsible. They were asked to leave the big bags on the first floor, only bringing essentials up to their room. They were asked to lock the door and turn off the lights. The door was locked, and lights left on. I will continue to consider late checkins, but only when they request as part of the initial inquiry and are willing to communicate fully about what this means for them.