I booked a 1bdrm at SSR at our 11 month mark. At 7 months, switched us to VWL. And at the same time, waitlisted for a 2 bdrm std view at BWV. Nothing has come through at all on our waitlist. I have it pushed out to 7 days before but I'm not hopeful.
I did ask about how the waitlist worked and the rep at MS told me that if someone cancels a ressie, they never even see the room come back in, that the computer automatically pulls it if there is someone on the waitlist for it. And they work their way through the waitlist so if someone is before you, they will get it first.
We were down for Jersey week last year and it was fine during the earlier part of the week but really bad on Friday/Saturday (of course, it took me a while to realize that it was Veteran's Day and I'm sure FL schools were closed). So I expect to do as much as possible early in the week and whatever we get to at the end will be a bonus.