First of all, if you are really going to go no matter what (maybe you already have non-refundable airfare, for example), you should have a back up plan - probably a cash reservation somewhere.
That said, I'd give up the earliest of these criteria:
1. Deadline for cancellation of the back up plan. I wouldn't want to pay a penalty for canceling my back up plan.
2. My banking deadline. If the waitlist didn't come through before my banking deadline, I'd bank the points (assuming I wouldn't need them before the end of my use year) so I wouldn't lose them if the waitlist didn't work.
3. If my back up plan was a reservation at another
DVC resort, I'd consider giving up at the 31 day mark if my waitlist reservation would use less points than my existing reservation. It would make me crazy to have a few points in the holding account. I would decide if getting the waitlisted reservation was worth losing the holding points (since I probably would not be able to use them).
In your favor: SSR is the largest resort and is most likely to have movement. IMHO, your chances are better than if you were waitlisted for any of the other resorts.
Not in your favor: You need several days and one of them is New Year's Eve. That night sells out faster than any other night of the year and there is no way to know where you are on the waitlist.
Advice: If you have a back up plan for lodging, call periodically and see if any of your days are available. If so, book them and change your waitlist. MS no longer allows us to waitlist for individual days and the chances of getting a single day are greater than getting a whole week all at once. I strongly suspect NYE is going to be the biggest challenge.
If you can (after considering above factors), stay on the waitlist past the 31 day mark and call several times a day if you get to the 7 day mark. (There are no waitlists once you get within 7 days of arrival. If you still want to get in, you have to call and hope to get lucky)
I agree with MS - there should be some movement later this fall and especially at the 31 day mark. Hope it's enough so that your waitlist comes through.