Thank you, we are definitely flexible. Kids are grown. Beach House and Windward Pointe, did you feel they are to off the beaten path and do they have shuttles?
With KW being a 2 mile x 4 mile island, the beaten path can't be too far away. BH and WP are located in New Town - SH is located in Old Town. The vast majority of KW visitors want to stay in Old Town as that is where the majority of activity (shopping, restaurants, bars, historic sites, etc) is located. There is some availability at SH, however SH only has 40 units and has a high percentage of owners that reserve their week - so it can be a challenge to get a reservation. Note that SH has studio, 1 bd and 2 Bd units - BH and WP only have 2 bd units. If it's just the 2 of you, a studio would be a better points use that the 2 bd units of BH and WP. Note that with SH being the 1st Hyatt TS property, due to the unit layouts, it's studios are the least desirable in the system. BH and WP are almost twice the size of SH - so combine their size with their location in New Town, there's pretty much always availability at BH and WP. BH and WP do not have shuttles to Old Town. The prevailing concept is that you don't need a car/transportation if staying at SH, however if staying at BH and WP, a car/transportation (cab, Uber, bus, bike or scooter) is needed.
What/were you buy depends on how you want to travel/use the Hyatt system. If you want to travel to a different location/property each time and are flexible in your schedule, Tucsonadventurer is correct, buy at Pinon Pointe as it has the lowest maintenance fees in the HRC system. If you're looking to use the HRC system as a way to be in FL in the winter, buy where you'd spend the majority of your time. FYI: Weeks 1 thru 17 are 2200 point weeks in KW - your mileage with 1880 points will depend on how (studio vs 2 bd) and when you travel.