I think it's important to understand how waitlist works, because it's not necessarily linear like a ride queue. It's more matrixed. You can waitlist whatever you want, but the more days waitlisted the harder it will be to match.
I'll try to make a very simple example.
You put in a waitlist for Sunday-Saturday, Kidani Savannah View Studio.
Joe has a waitlist for Sunday only, Kidani SV Studio.
Mary waitlists Tuesday-Wednesday.
Bob waitlists Thursday.
Sue has to cancel her trip, which was Monday-Saturday.
The waitlists filled by this will be Mary and Bob, skipping over you and Joe entirely. Sue's trip did not include Sunday at all. So the waitlist skips you, fills Mary and Bob, and puts Sue's Monday, Friday and Saturday back into open booking.
Now, if Joe, Mary and Bob were ahead of you, and Sue canceled a Sunday-Saturday, you'd still get nothing, because since their dates were included in Sue;s stay, their requests would be filled first.
Your waitlist has to match in its entirety, and you have to be front of queue when the entire stay becomes available.
The shorter your waitlist, the better chance you have at getting it, with the wild card being category size. Any category might happen, but it's not visible how many people are waitlisting any given category or for how long.