We've been waitlisted for late seating 3 times and have cleared the waitlist every time. We often book with the last minute *GT rates after main seating is full and go on the waitlist. I believe part of the reason that we have been so successful in having the dining time switched is that we have young kids. One of our kids was under a year old each time. We are waitlisted again on our upcoming cruise this fall -- kids are now 4 y.o. and 18 months old. I do think Disney makes an effort to put the youngest cruisers in the first seating when at all possible. I don't know your circumstances, but if you have young kids, that may be a leg up for you.