Improving bookings mid-week

The ideal way of dealing with orphan nights is to prevent them from happening in the first place… But that's more of a master class (involving dynamic minimum night stays, check-in and checkout restrictions, etc.). 

To help fill gaps after they're created, you can configure a scheduled message for something like a few days before a guest’s arrival, and use the conditions “the night before is available” or “the night after is available” … to ask them if they'd like to arrive a day early or stay a day late. From that point forward, it's not automated, but it’s more of a conversation; if the guest says yes, you would send them an alteration request.