Conditional Triggers -such as upsell adjacent unbooked nights

Many guests will extend their stay if they receive a discount for an unbooked night adjacent to their stay, and the owner/manager gets to increase occupancy and revenue. It's a Win win. Doing this manually is very time consuming. A conditional trigger that can analyze the calendar and ask the guest if they want to extend their stay or check in a day early would be amazing. 

This already exists, as a trigger option: