During my Navy career I made port calls in Hawaii no less than 23 times over a span of 15 years. Some stay were nothing more than 2-3 days resupply stops, other times I was there for a few weeks. The islanders have their cliques, their customs and their societal rules and the "Howlies" (a derivative of the Hawaiian word 'Haole' which translates to 'foreigner') are not easily welcomed into this life.
Hawaii is far and away the most expensive place in the entire country, including Alaska. It is so expensive that military families stationed there are subsidized a huge amount of money on a monthly basis just to be able to afford housing and food costs, not to mention gas.
I don't care if I ever see Hawaii again. I got to do all the tourist things and after a few stays when I became very familiar with it I could go blend in with the locals on their beaches and do some of the things unknown to tourists. But I was bored with it after awhile; you can't get away from it, you can't escape it. I think you have to be at a very specific place in your life where travel and adventure and escapism is no longer a priority to live there.
Here's an idea though... when I made the decision to retire from the Navy, I literally put a map of the US on a wall and threw a couple darts at it. I ended up moving from San Diego, CA to Pleasant Garden, NC. Had the Navy move all my stuff cross country while I drove and took 2 weeks crossing the country seeing all the stupid stuff few people stop to see- Tombstone, AZ (OK Corral), Cadillac Ranch in Texas, Gateway Arch in St. Louis, some Presidential birthplaces, etc.
I'm very close to talking the wife into staying where we are now for just 3 years before we do the same thing...