There was a commercial glider operation on that Island once. On the
strip that is near Lihui on the southern tip. I flew both the Pawnees
and the 2-32s taking turns. We were too far away from any ridge and
the job was boring, we would tow a mile up above the low clouds that do
not have lift and glide down slowly sightseeing.

My suggestions a first learn the sport well. Then you may look at
the whole thing differently.
If I would live on the Islands I might not do the sport there. A self
Launching sailplane would work that you might fly off any airport and
reach distant ridges or wave. There was a Stemme stationed at Kahuluhi
for a little while. The owner was starting up another com Operattion
and since I wanted to see the islands from above once, I bought a one
hr ride or a little longer. We climbed up
to the top of Haleakela. I think It was 11500ft. I thought, with this
altitude and the performance of the ship we could reach the big Island.
so we turned off the engine and made a long glide there.
It was quite erie to sit high over the Pacific flying off that
altitude. On the big island we turned on the engine climbed up to
Observatory turned the engine off again at about 14000ft and made a
final glide across part of the big island, the sea and half of Maui
back to Kahului. During that whole flight there was never any lift! I
think the Islands have other sports that makes them great!
Soarski