The other thing about waitlists is that they are all-or-nothing. So, if you have a five-night waitlist, and four of those nights suddenly become available, you will not get them.
So, another strategy is to waitlist night-by-night in the easiest category of the room size you can find (which is probably SSR Standard). Waitlist the first two nights, when one of them matches, add the next night and so on. Once you build your trip, you can play the same game with a "better" resort if you want to. But, I would not turn my nose up at SSR/OKW unless I would rather not go than stay there.