Plan on doing exactly this if I ever sell my house. I've had enough of cold winters and crappy waves.............
I hear you man, cold weather and no waves means nothing else to do unless you have access to cash. i.e. mommy and daddy's money, or you have extra cash yourself with limited responsibilities. I lived in honolulu for about 4 months and I loved it. I came back for alot of wrong reasons and a couple of right ones. I have been dying to move back, but now I have a house, a child, another on the way, and I'm strapped for cash.
I know tons of guys who have done this. most of them were transplants living in socal. then they moved to maui etc.
I have thought of moving to hawaii;but after relocating from maryland to san diego, I feel like I hit the jackpot. great surf everyday. perfect weather (better than hawaii). the water in cali is 65 to 70 most of the year and bottoms out at a frigid 58 degrees.
so, I guess what im trying to say is this. I have never met anyone who has moved to hawaii and stayed there for good.
its hard enough to move from east coast to west coast. staying in touch with family is hard enough.
being stranded on rock in the south pacific makes things even harder.
so do your research. can't hurt to try.
im just saying most people do hawaii as a long term experiment and then go back to where they r from. its too big of a culture shock for people from cali even. so east coast to hawaii might rock ya.
go to hawaii, but if that doesn't work out, try out the west coast. consistent surf year round. and its all cities and jobs and reality.