More from the stack of negatives which recently turned up in the last of my dad’s papers, most featuring Hawaiian Airlines planes over various parts of the islands.
In this shot, the HAL DC3 is flying over what appears to be the area that later became Joe Pao’s Enchanted Lake subdivision.
I’m not familiar enough with this part of Kailua to recognize all the landmarks.
And the area, of course, has been completely transformed by development during the period from 1960 to the present.

Also see:
Waimanalo about 1949: Another view
Waimanalo: Another look back at Hawaii around 1949
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wow, it actually looks Enchanting!
Having a lot of trouble with this. That is Olomana, but from the back side, third peak. First peak is on the left. So seems to be coming in from Waimanalo side.
That is the Pali highway running parallel to the trailing edge of the wing on the right and the bend just as it enters Kailua. It looks like the water reservoir on the hill just above. That reservoir was probably pretty new then but has since been abandoned and (I think) demolished. Hamakua Drive now runs along the base of those hills heading towards enchanted lake on the left. The beginning of Keolu Hills is at the extreme left. Wainanalo is the light patch just behind.
That is indeed Olamana , first peak on the right and third peak on the left. The first peak is the more massive with the third peak pretty much just a blade. You can see the very distinctive, very narrow trail to the third peak which has claimed so many lives.
Kailua Road can be seen as the line of trees in the lower part of the picture and making the turn toward the beach at lower left.
Lots of development since that picture.
Worse, or more dramatic, transformations might happen than Joe Pao´s 1960s Enchanted Lake subdivision – and actually they have.
See this reference in the current issue of The New Yorker magazine about a ghastly seismic transformation of the Pacific northwest in the year 1700 that Lewis & Clark a hundred years later completely overlooked:
http://www.newyorker.com/magazine/2015/07/20/the-really-big-one
These are a treasure! I hope you can put together a collection to show at a museum.