UPDATED! What are your best Wait List Tips/Tricks?

Example... I want to stay in late Sept (21-28)
I really do not care where, looking at the usual larger resorts like OKW, SSR, AKV.
There are several 1 night or 2 night rooms available at the moment.

If this were you... how would you construct your wait list options... the full time at 2 resorts. Break it up into 2 smaller stays and waitlist 2 reservations at the same resort?

UPDATE...
So far I have been able to secure all but 2 days at Kidani Village.
I have Sept 21-24 and Sept 26-28 booked... and waitlisted Sept 24-26.
However, I have found both of these by periodically checking the site randomly over the past few days.