Hi Tommy...fun list! I have not played on Oahu either through about 8 trips to Hawaii (did the WW2 tourism thing as a young teen), although I'd like to acquaint myself with Oahu golf-wise some year.
I find my opinions pretty close to yours with a few nits to pick, although much of it is because my experience is about 15 courses total.
My top three would be Kukio/Nanea/Plantation, but the order depends on the day. Plantation is probably #3 most days. I have not played the Challenge, but plan to play Mauna Kea in November. I have played Kukui'ula, and it makes a case for state #4. I have a higher opinion than you of Wailua after about 5 plays, as I think it's really a gem. One can get caught up in the "its a gem for the money" argument, but I've always thought it's really neat outside of that.
I have not seen Kohanaiki or Hokulia yet, so not sure how they fit.
I like Poipu more than most, but I think you have it well-placed in the pecking order. I played Hualalai a couple years ago, and I agree it's a bit of a dumb-blonde type, but it was a nice place to play.
The Prince is a conundrum for me...beautiful, wacky, wild...maybe only a good match-play venue? I couldn't get my head around it in terms of fairness, but I'm not sure that being fair was the goal! I only played it once, and it was during the Northeast US golf off-season, so I had a very tough time.
On the order of locals, the Dunes at Maui Lani is worth a try (think Maui's version of Puakea), and so is Pukalani partway up Haleakala. There's a neat par three there where you can choose a green on the far side of a canyon carry, or an alternate green down in the canyon itself...bet you can't resist hitting a tee shot to both!