We've been waitlisted several times and I'm happy to report being pleased with the results. Things tend to happen very fast between 31 and 40 days before your desired check-in date. The automatic confirmation day-by-day waitlist works best if you can set it up that way. Good luck.
Just got Vero for Easter Sunday night via the wait list. I had a cash ressie there as a backup, and requested automatic confirmation. That means they will book you as soon as it's available and use your points, and then let you know via snail mail. I actually found out first by logging into My DVC and checking my upcoming trips. The snail mail arrived a few days later. Good luck!
By day-by-day I mean you confirm the days you need ONE AT A TIME as each day becomes available. This works better and I believe your chance for success increases exponentially over the method where you wait until all of the days you need become available ALL AT THE SAME TIME. To do this though, you need enough points available to keep your backup less desirable current reservation (2 bedroom + a studio) while you work towards confirming each of the days you need in the Grand Villa. If you have enough points available to confirm the Grand Villa AND keep your current reservation call MS and ask for day-by-day automatic confirmation.
I just read your other thread where you state "I don't have enough points for a Grand Villa anywhere else." From this statement I get the sense that you need the points from your current reservation (2 bedroom + a studio) to book the Grand Villa. If this is the case, day-by-day wouldn't work for you unless you're willing to cancel the current reservation hoping all the days you need in the Grand Villa do in fact become available. Doing this though can be risky as you might find yourself with no place to stay if the waitlist doesn't clear.
Hmmmm...maybe I should make a cash reservation for the Thursday night (2BR) that I am waitlisted for at HHI in July. This is my first experience with a waitlist too. If it wasn't high season, I wouldn't worry about it so much.
I'm nervous about our waitlist for a 2BR BWV for August. Initially I had 2 nights wait listed but within 48 hours one night came through. I have my fingers and toes crossed for all on a wait list!