Hawaii planning help requested, so forgive me for all of the questions that are about to come...
I jumped into this game with the goal of offsetting costs to Hawaii in Sept 2022. I've searched the boards, read trip reports, and created a table of notes on excursions and places to stay. I believe I read that I need to be prepared to make our reservations this coming fall (Sept. 2021) especially since we'll be using points. I'm trying to figure out what kind of points goal I need. Only 3 of us- myself, DH, DD13. I'm initially planning for 2-3 week trip.
Currently 3/24
9/20- CSP/CSR
12/20- Hyatt
Also, have a Disney Visa and Chase Freedom that we've had since the early 2000's I believe.
I'm working on Hyatt points now for Grand Hyatt Kauai and DH will have enough points to cover Marriott Ko Olina. Based on the Hyatt, it looks like 25K per night for a standard room, but I'm aiming for Globalist and elite nights to get a suite. Will this change my points goal?
Is Hilton a must? Should the Aspire come into our plans at some point that we could utilize on this trip?
I'm sitting on a personalized mailer offer (expires 2/28) for an AMEX Plat w/ a 125K SUB, but I'm a brand new player to AMEX and unsure how this can benefit the Hawaii trip. How can this help toward this trip?
Flights- we're flying from the East Coast. My husband has priority w/ AA and I had plans to work toward a CP for Southwest at the end of this year. Is there something different we should be considering?
If you've made it this far, thank you for reading! I guess my ultimate question is how can I best use this year to earn rewards AND my remaining 2 slots?
@SouthFayetteFan gets huge props for helping in the wings for months to even get me to this point, but I thought I may give him a break and share the questions with the masses

Thanks, y'all!