I think the largest category of rooms is Saratoga Standard---it's also the resort that people are trying to "upgrade" out of most often. I'd be inclined to do it there, and waitlist it day by day. So, WL the 23rd and 24th separately. When one hits, add the 25th. Also stalk the site.
The advantage of day-by-day WLs is that you only need one day to be free to snag it. If you waitlist the entire trip, the whole trip has to come free at the same time. So I think that maximizes your chances, but there might be other strategies I am not thinking of.
With the Holding deadline coming up, I think you probably have a decent shot at getting something.