USUHS2008 said:
3) Are you willing to pay for a high cost of living? It's as expensive to live there as Manhattan or Washington, D.C.
I disagree with this. It's expensive short term, but if you're living there a couple of years, cost drops dramatically. You learn the ins-and-outs of where to shop and how (canned goods at one place, produce at another, etc.) and get local connections (priceless for things like cars/apartments, etc.).
Hawaii's very expensive short term. If you're living there a while, it gets a lot cheaper if you enjoy the simple pleasures.
USUHS2008 said:
4) Would the practicalities of moving everything by plane or boat bother you? What would you do about your car?
Not as expensive as folks fear. I moved a two bedroom apartment for about $1,200 to the west coast. A car goes for about $800.
USUHS2008 said:
6) do you have a spouse? Does their job travel well?
Very valid. Unless one's spouse is in travel/hospitality, expect jobs to be hard to come by. For any job, expect the salary to be much lower. I took a 35% pay cut for a comparable job to the mainland. Some folks take a larger cut.
Hawaii's a tough move, but the longer you're going to live there, the easier it gets. Three years is about the minimum I'd move there for, though...