I've never known
DVC to give out any info as to where one is on the waiting list. But we have seen many reports of people on the list calling DVC MS and inquiring, only to find that exactly what they were wait listed for was indeed available. The implication was that it had bypassed he wait list and had they not called, would have missed it. Also, as debbiepump alluded to, the wait list evaporates at 30 days out and a new one is started. Non of the existing people on the old wait list are carried over, you must call or email again to get on that list. At 7 days out the wait list is abolished.
There are actually several ways to wait list. You can ask them to call or to auto-confirm. And you can wait list day by day or for the entire reservation at once. One of the problems with waiting on the entire reservation at one time is that they will pass you by unless they have all the days. Say you want 7 days and they only have 6 of those days, they will simply go to the next person and will not save them for the extra day. Day by day gives you a much larger chance of success.