Well, I am sure a local will help you more then myself. But, I have been to 4 of the islands and have been to Hawaii a few times.
You realize that Oahu is a city. There is a lot you can walk to or take a cab to.
It is not inexpensive. I found the restaurant pricing on par with the better places of NYC. I could hardly believe my eyes at the Italian restaurant pricing......Whew!
They seem to have good hospitals, everything is up and current.
If you like city life, then the Oahu is good for you. From what I understand jobs are not a plentyfull supply. I'd have one lined up before I go.
If you like less city life, the Maui would be a nice location.
Kauai was my favorite, full of flowering blooms, and much greenery and waterfalls.
I didn't see many job opportunities on the Big Island of Hawaii.
I remember on one boating cruise the host said "you may want to live here, its beautiful, but......the jobs are not in big supply"
That would be your main concern. Housing costs are high, and rentals........I'm sure the Hawaii thread will have areas you can check into on that.
Dig deep into the Hawaii threads and find your answers there.......Good Luck to you.

The Wikiki beach ( swimming area )has rounded rocks that really require some sort of beach shoe to be able to walk on.......that was a surprise to me. But, they are needed for sure.