We often accidentally book them from the calendar and then forget to delete waitlist entry. Sometimes you get the embarrassment of reaching out to them about an appointment after you already booked them for one. A reminder about this would be super helpful!

I am open to almost any tools that would help manage the waitlist (bulk selection/deletion would be amazing!)

Perhaps not automatically, but match it and ask the user whether they would like to delete the waitlist entry for the current booking. I would get worried there are notes or other things on the waitlist that we might want to retain in some cases. Also not certain if there is a way to restore waitlist entries or search deleted ones.

automatically remove client from wait list when appt is booked on the date requested or date range