If you are an owner, note the request on the reservation confirmation. Those requests are processed in the order of the earliest date the waitlist request or reservation confirmation was made. Units are usually assigned by the Resort Manager about 1-2 weeks prior to occupancy.
If the requested unit will be occupied by an HRPP owner, then that unit is not available. If the confirmation is thru Interval, there is a very low chance the unit request will be granted. If the unit is provided thru rental, then no chance whatsoever.
It's best for HRC owners to make the request for unit preferences at the time the waitlist request is entered.
I would say the best units at Windward are the top floor units facing the ocean. Unfortunately those units are prone to a little more traffic noise.