Sometimes depending on when a guests books they get a barrage of emails that you don't necessarily want to send at the time of booking.
Could the Booking Field Trigger Criteria have more options for the Booked on Date?
Such as [Is Not] - [Today] or [Day of week].
There is a criteria “Arrival days from now” “Greater than or equal to” -> 1
Combined with your other criteria, wouldn’t that solve your case?