MS usually won't suggest a wait list position, because it will depend on how you are waitlisted.
If you are waitlisted for a BCV 1BR stay from 11/06- 11/11 you may actually be lower on the list for some of those dates that someone who got on the list today- even if you've been on the list for a month.
DVC won't save individual dates to complete a multi-day reservation. They may give you first opportunity to accept that reservation if/when all days become available at once but otherwise, those who are on the automatic-daily waitlist will have better success getting their individual days. If 11/08 becomes available today, the auto/daily member will get that date. If 11/10 becomes available tomorrow, the auto/daily member will get that also ...
If someone cancels a reservation for 11/06-11/11 today, you would likely get that reservation, it you were first on the list and were available when they tried to call you on the phone- otherwise, it would go to someone who indicated they will automatically accept the dates.
Bottom line is , MS won't let you know where you stand on the list because there are several variables that affect the answer. There have been times, however, when MS actually closed the waitlist for certain dates because they knew there were more already on the list that likely cancellations based on past history.
The waitlist does work, but it might help to allow MS to grab each day individually as they become available. You might end up with a middle date where you'd need to move though- so that is the risk.
Good luck!