Having one of the rooms with no A/C in the 2nd bedroom can be nice if you're not using that bedroom, because the dining area will have A/C. Of course, most the time you won't need A/C in Poipu, but when the trade winds stop working, it can get hot and humid.
The rooms that don't have A/C in the second bedroom are located in buildings that have a convex curve toward the ocean, such as Building 2, 5, and 9. At those bends there will be a unit that is narrow in the front and wide to the rear. In those units, the second bedroom will be at the rear, and will not have A/C. (But as you noted both the master bedroom and the dining area will then have AC.)
In my mind, the bigger issue with those units is that the window in that second bedroom opens to the outside walkway on the back side of the building. Since the room doesn't have A/C, it is often necessary to have that window open at night. But then you have people walking right past that open window. And you know, if wind is blowing the curtains are moving, etc.
I don't mind those rooms if it's just DW and I. But if you need to use both bedrooms, the arrangement is far from desirable. So when we have more people, I put in a request to not be assigned one of those units.