Planning move to the islands

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Best wishes, keep us posted!
Don’t overlook working for government jobs as a possibility, either state or civilian contractor at the military bases, or the online Jobs listings. My Mom used to work Human Resources at West Point and although the pay is not as good as non-govt, the opportunities can be very interesting.
 
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Things certainly change over time but a few years ago you could rent a condo in areas south of Kona/Kailua very reasonably - when the US economy tanked there were a lot of them available - a monthly rate was about 1/2 the 4x weekly vacation rate with a longer commitment.

Similarly I often see good deals still on condos in the Kihei area of Maui since there's a lot of them in one area across the street from the beach.

assuming you can find work on either island...
 
Similarly I often see good deals still on condos in the Kihei area of Maui since there's a lot of them in one area across the street from the beach.
.

I stayed in one of those a few years ago and it was pretty much "put on your gear, walk across the street and into the water." :)
 
If you come to the big island check out the local craigslist. They have a lot of job opportunities listed that are really pretty good. You can also look me up if you want to learn some local shore diving. I run a little shore diving operation here and would be happy to show you some of our local spots. www.divingbellscuba.com
 

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