New field needed? How to to alert cleaners about back to back cleanings?

My new cleaner wants to be alerted when a new booking creates "back to back" cleanings.

I don't think I can do this with existing OR custom fields in my normal new booking alert email, because the "Available Adjacent Nights" field does the opposite of what I need. That field has no content when there is no gap, it only has content when there are >0 adjacent nights.

I think a new field is needed that will have text like this:
- This booking DOES NOT require back to back cleaning.
- This booking requires back to back cleaning on arrival 7/4/2018
- This booking requires back to back cleaning on departure 7/8/2018
- This booking requires back to back cleanings on arrival 7/4/2018 and departure 7/8/2018

I see that I could create a trigger based on no gap, but that means I have to send up to three emails to my cleaner for new bookings
1) the new booking created alert that states the dates
2) if no gap prior to booking
3) if no gap following booking

I don't think I can combine 2 & 3 into a single email because the cleaner wouldn't be told where the no gap exists (prior or following or both)

Am I missing some easier way to implement this with existing OR triggers/custom fields?