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Where are you moving from? (If from the west coast you will have more options than from farther east.)
Will you be staying permanently, or for a set period of time? On which island?
If you were to get rid of your stuff and buy new, do you have the time and means to sell it for a reasonable amount? That can be more difficult and time consuming than you might think. Ditto the car - it's not easy to get blue book value on a private sale (at least not where I live), and you will not get very much from a dealer. On the other hand, if you were thinking of trading in soon anyway, it's simpler to sell and buy.
(FYI, I'm packing for our move right now, we're moving from NY to Kauai, moving three households with a 40' container for our house and business, and a 20' for my mother's house and my sister's; one car; and two cats. We are using Matson to ship the stuff, Horizon to ship the car from CA (driving it out there), and local movers to load the containers and wrap the furniture. We're packing the boxes ourselves, we are paying our own costs. Our container will be packed on 7/15-16, and we leave for our x-country trip on 7/18.)
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