MS really can't tell - it isn't as simple as we might think. It really isn't a sequential "list".
For example, someone could be waitlisted for June 1 -5. Someone ese might be waitlisted for June 3-7, and someone else just for June 2. Assume they got on the waitlist in the order I listed them. Now if June 2 - 5 all of a sudden becomes available, the third person gets his waitlist even though there are 2 people ahead of him for that date. MS will not hold available time for you waiting for the rest of your dates to become free.
Now if you imagine all the different combinations of waitlist requests, yo can see why you need a computer to figure it all out. And FWIW, for some times of the year for some room types & views, even being first on the waitlist doesn't mean you'll get it.
Best wishes -
