wls23 --
We just bought at SSR last October and instead of going to Disney we decided to do HHI instead. When we called MS to book our HHI trip it was in April, only a few months before our planned vacation dates. We wanted 3-4 mid-week nights in a studio. We were told by MS that no studio was available from June thru beg of Sept. We had no idea that HHI booked so quickly, and our only option was to be put on a wait list. We did a wait list for 3 nights for any Sun-Thurs in June/July/Aug.
After inquiring on these boards about contacting MS every so often about the wait list, we were told that 'IF' something became available, those on the wait-list would be identified immediately and MS would contact the person asap. From what I've been told by MS and here on these boards, by calling in every now and then, does not increase your chances for you reservation unless your dates are not in the MS wait-list. Said, differently, if your dates are on the wait-list, calling in every so often does not increase your changes. When the dates become available they will look at the wait-list first; not someone who just happens to call in looking for those same dates.
In closing, the wait-list DOES work even when it seems hopeless....just look at our count-down clock (we were called by MS two weeks after being put on the wait-list for HHI).
Good luck !