@Saucerking27 Your answer can be found on post #1952 of the waitlist thread:
http://talk.collegeconfidential.com/prep-school-admissions/1300302-the-wait-list-p131.html
Ultimately, you cannot bank on getting off of the waitlist as the chances of getting off of the waitlist is incredibly slim and in some cases zero if the school overestimates its yield. The only thing you can do is accept a spot on the waitlist and move on. I understand that this is a tough and disappointing outcome, but if you really want to go to boarding school, you must find a plan-B, I have linked boarding schools with rolling admissions/that are still accepting applications that you can apply to:
http://www.boardingschools.com/find-a-school/quick-lists/rolling-date-application-deadline
The answer you receive is not going to change by asking the question more than once. If you want to hold onto hope on getting off the waitlist, that is your choice but if you truly want to go to boarding school I suggest you look at the above link.