There is usually no way to know your position on the wait list. There are a couple of ways to use the waitlist. One is to request your entire stay and have MS contact you to confirm when the reservation becomes available. Realize that MS does not save available dates towards a reservation- you will be contacted only when/if the entire reservation becomes available at one time. You will usually have 24 hours to respond to the offer.
The other wiatlist method is to ask MS to automatically confirm each day of your stay as it becomes available. That way, they can automatically add days to your stay when they get a cancellation. The only problem with that method is that you could end up with missing days and have to move resorts or room types. My experience is that the method has always worked to fill my request, but you could end up with disappointment. By using the daily/automatic waitlist, it's possible to get your reservation ahead of someone who went on the list earlier than you, but is waiting for their entire stay to come thru.
Good luck!
