I wouldn't consider Wyndham, unless you love Princeville, but the only resort worthy of using points is Shearwater. Shearwater has gorgeous units, but to get a penthouse 2 bedroom, it's 500K points, or around $3,000-3,500 to stay a week, depending on the cost of your maintenance fees on the points. Shearwater has a very small pool. It's really about ocean views.
I don't like Bali Hai (we own there and are not fans of the cramped buildings). You already have Hilton for Waikiki. Hilton has Maui, Wyndham has nothing on Maui. Hilton is adding a lot of buildings to what they already built. The resort is going to be massive.
Big Island is covered well by Hilton. We own Wyndham and still stay at Kings'Land and the other Hilton resorts. I love the Hilton experience over Wyndham. The one time we stayed at Wyndham's Kona Hawaiian Village, or whatever it's called, we had a huge issue with roaches. Big turnoff.
We own Westin Ka'anapali, and it's not cheap, but it's worth it. We can lockoff our unit into two sides and use each side for back-to-back weeks. The reservation system at exactly midnight to book what we own for dates we need is a nightmare. Marriott hasn't improved it at all. There are so many people who are trying to reserve, and it takes forever.
As
@CalGalTraveler stated, learning multiple systems can be very confusing. I know all about it. Add in the exchange company rules and it gets ridiculous.
For our kids, we are able to trade into Westins to get island view units through Interval International. The kids like to stay at Westin but don't care about views. We are there at the same time, so they visit our unit for some meals and views, and of course the pools are fantastic. But if you want a guarantee of view and availability, buying is important. Island view units are not that expensive to buy.
You could buy a good trader with Marriott, a platinum week that can be locked off into two units and try exchanging. I enjoy it as a game to try to get accommodations. I occasionally see something online that I hadn't considered.
What part of Colorado do you live? We live in Thornton.