Scheduled messages not sent the day before departure for 1 night stays?

[Moshe2]

I noticed that when I schedule a message to be sent the evening before departure, it is only sent when the stay is 2 nights or longer.

Does anyone else have this problem?

[Inna22]

@Moshe2 city of Chicago no longer allows one night reservations but I wanted to give your question a bump. 

[Moshe2]

This problem just surfaced again with my most recent guest, a 1-night stay. The message scheduled for 1 day prior to departure was not sent. How am I supposed to remind my guest about checkout stuff with enough time? I tried setting it to the morning of, but then my guest complained that I should have sent it the previous night.