I have successfully stalked two reservations in the past year. Availability changes constantly, and it is kind of fun to see just how often it changes. I was checking at least four or five times a day--whenever I had a few minutes.
The first one was a three night stay in a standard studio at BLT for Wine and Dine race weekend last year. I can't remember the exact details, but I probably cancelled and booked reservations a half dozen times. I was eventually able to grab one night in a standard, and two nights in a theme park. I then waitlisted the nights I needed to get all three nights in the same room, and eventually all three nights in a standard studio at BLT.
The second time, I was able to piece together a four night stay at CC less than three months out. I originally was just going to do three nights, and actually got that on a waitlist. I decided to add a fourth night, and put in a waitlist less than 60 days out. I continued to check though, and actually snagged the room I neeeded by stalking before the waitlist could pick it up.
So, keep checking. And good luck.