We bought last year on 6/19 and tried to book T-giving on 6/20...had to W/L (of course)...but first a one-bedroom and then a studio came through...took about 6 weeks, as I recall.
What we did: booked the nights that were available (Tuesday, Fri, Sat, Sun) at our home resort, SSR...W/L'ed Wed & Thurs in either a 1-BR or a studio--said any resort would be fine...at the time you chose between MS calling you when a W/L came thru, or doing it on automatic...I chose to be called...also, and this is important: W/L each day separately! Then, I made a cash reservation at ASMu, so we'd for sure have a place to stay Wed-Thurs if the W/L didn't work...
First Wed came thru--first a 1-BR, and then a studio...T-giving itself came thru, in a studio, shortly thereafter...my recollection is that I made a couple of changes as various W/L options came through...I know I could have booked us into OKW--probably I had us in a 1-br at SSR and then a studio at OKW came through and I chose not to move us...then the studio at SSR came through. I know we wound up in one studio for the whole vacation at SSR...I canceled the cash reservation at ASMu as soon as the W/Ls for the whole vacation came through...
SO, very definitely use the W/L...I'd say your chances, while not 100%, are good...especially this far out...
Pixie dust to you...