It has an "Okanagan valley" look to it... (or "Okanogan" if we're on the USA side of the border)
Penticton?

I think that you have taken us back to the far east.

Around the Great Lakes possibly.

You speakin pigin ?

SE Asia...…?

Sea of Japan ?

No to Japan. These southern skies once graced by a WIWOL of high regard, one who takes to the air(sounds like?) no more.

Southern skies.

Yes, I've been looking antipodean but trying to make the other clues fit, especially WIWOL.

Sounds like?

Can't find anyfink in Oz or Kiwi.

One took off 10 minutes ago, another due to land in 20. Not military.

Really...….!

Pucon Airport in Chili
with nearby Lake Alumeni?

OH if correct

SLB

He says Pucon, you reply Upson.

wtfo ?

They don't speak English in Chile or around there apart from the very south of Argentina.

South Africa?

I looked there at Aliwal in response to the WIWOL clue.

Pucon of course, thought that I had changed it. The WIWOL clue, obviously you do not ken. Air ( sounds like ). South Africa the wrong way from Chile, go West and South. Field active at the moment, Cessna 208.

For those not familiar with RAF-speak, When I Was On Lightnings. The individual who shared these skies commanded a Lightning station.