beckoa, I agree with pretty much everything you said. No upgrade at the OC (even when I was platinum), small upgrade at Wailea to better view on a points stay. (IIRC Bruce once posted he was upgraded to a suite at Wailea on points, no such luck for me.)

The OC has kitchenettes with microwave, toaster and stovetop I think, so much more ability to cook, and a blender for our own drinks (we stop at Costco off the plane and buy rum and mix). Wailea was just a room, had a frig and coffee maker I think. I think there were some grills at Wailea too (the OC has a bunch) but I can't remember for sure. Since we swim in the pools, not the ocean, the beach is for walking and Kaanapali is pretty long, there's also a paved walking path right next to the beach that goes pretty far, at the north end there's a hotel (Sheraton?) that has a cliff diver at sunset, and you can walk further north by crossing a golf course to another paved path.

The Wailea had a luau 3 or 4 nights the week we were there, our room was right next door, so we saw it for free, if at a short distance. After a couple of times, the novelty wore off and we ignored it

Wailea definitely felt more "resortish" and seemed quieter and less "kid friendly" but because of no kitchens we spent more on food and drinks, and had to drive more to get to non-hotel things (although there is one mall right next door with several restaurants).

I'm ready to go back to either one.