Y'all are so helpful!! Thank you for helping me sort through this!
Based on what I've read Kauai is going to be the best match for us as well. I'm settled on the Grand Hyatt for that one and have the points to make the reservation.
Reviewing all of the notes and excursions that you and
@wanderlust7 have shared, Maui is definitely the second longest stay but I'm torn there on where to stay.
Good to note! I have the MRs to transfer over to book the Grand Wailea and reading the trip reviews are quite helpful. We could also get an extra night here for 5 nights.
However, looking up the Wailea Beach Villas through Hyatt that's much more suited to our style and comfort level. BUT, it's 244K points

for only 4 nights which feels like a lot although that's exactly the type of room we'd be looking for. One line in your review of the Hyatt Residence (people, people, people) took that one right off the list! It's so silly since we have the points to feel like I can't "spend" them but the whole reason I entered this game was to offset costs for this specific trip
Also, I'm not settled on the best route to fly in and out. Do we go to Oahu 2 nights at the beginning, head to Maui, then finish at Kauai? Or reverse and go Kauai, Maui, Oahu? Or Oahu, Kauai, Maui? Part of me wants to start with the touristy since we'll be adjusting to the time change and can be up and going and then end with the relaxing.
One I get the route in order, then I can go ahead and get the reservations made!