Which town? The town most people think of is Cabo San Lucas but the Hilton and the airport are closer to the town of San Jose Del Cabo.
The Hilton is located on in the tourist corridor (hotel zone basically) stretch of road by the sea connecting Cabo San Lucas and San Jose Del Cabo.
It is a 12 min drive from San Jose Del Cabo and a 25 minute drive from Cabo San Lucas.
The airport is north of San Jose Del Cabo and a 30 min drive from the Hilton
The Waldorf is right at the bottom tip in the downtown area of Cabo San Lucas, near the marina and the famous Arch.
You can walk to things from the Waldorf you cannot from the Hilton.
The airport will further way from this property ; about 45 min drive away
The 2 hotels are about 30 min apart by car.
Worth noting, you can swim in the ocean water at the Hilton but not at the Waldorf as the Waldorf sits on the Pacific side of the tip with very dangerous rip current right at the beach.
As far as availability, I don't think there are any rules. I see some one night available at 80,000 pt's next month for the Hilton which I assume is the base rate so would say not accurate but that likely greatly improves your odds or may be the only way to book far out.