If you decide to stay at Wailea, I'd recommend one of the ocean-front rooms. (Note that they have a few categories - "ocean view", "premium ocean view", "ocean-front".) The ones I'd recommend are ones that are the closest to the ocean and have a balcony or lanai. It's amazing to go out on the balcony and watch the sunset. I think you can upgrade to these rooms if you're using points.

Honolulu -- Leonard's is pretty famous for their malasadas (a Portuguese donut-like pastry). Marukame Udon has some some great udon if you like Japanese food.

Kauai -- if you like it, I highly recommend exploring the hiking options. Some of the most beautiful views and trails I've ever seen. (Some are very difficult though.) Hanalei Bay I'd recommend as well -- small but gorgeous.