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I'd move to Hawaii in a heartbeat. My wife, however, has vetoed it as being too far away from her family here on the East Coast. I even told her I'd be willing to give up the racecars and motorbikes, and she didn't bite.
I think the biggest obstacle for most people is island fever. Can you stand to live so far away from the rest of the U.S.? That's a personal decision. Personally, I think I can. Most people, probably not.
Cost of living is just a detail item. You deal. Everyone there does. Yeah, everything's imported and costs more. But everyday you wake up, and it's paradise.
If you do go visit, I highly recommend picking up the tourbook "Hawaii Revealed," or something like that. It's paperback, blue cover, with a cartoon map of the Big Island on the cover. (There's a separate book for each major island.) Lots of recommendations on stuff to do, restaurants, hotels, beaches, etc. Interesting historical vignettes for cultural perspective. And it'll show you the diversity of the island.
Worst case scenario: you move there, hate the island fever, and move back to the mainland in 4 or 5 years. In the meantime, you've had the opportunity of a lifetime, and you're culturally richer for it.
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1987 Venetian Blue (looks like grey) 930 Coupe
1990 Black 964 C2 Targa
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