This is going to surprise a lot of people, but after spending nearly 3 weeks there on a work trip, one of the last places in the world that I would want to live is Honolulu, HI. Yeah, early on early on in the trip you are mystified by just being in Hawaii, and you can't believe just how beautiful the place is. Then, as some time passes by, you begin noticing things. It's absolutely crowded and the traffic tends to be worse than in New York City (particularly on I-H1). It's far dirtier than anyone would ever realize. Waikiki is becoming run down, or at the very least, is showing its age (every resort on that beach looks at least 40 years old). It's industry and ports are either mixed in with or at least in plain sight of its touristy areas. There are a lot of rough areas in town, a lot of them close to Waikiki. It's hot and humid all the time, it's expensive as hell, and quite literally, once you're there, there is no escape.
Look, I'm not saying I didn't enjoy my visit there, because I did. The North Shore of Oahu is absolutely beautiful, Diamondhead gives you the best and most striking view of Waikiki, Mauna Loa Trail might be the most beautiful nature trail I've ever walked, the Pearl Harbor visit was mandatory and sobering, and the U of Hawaii might just be the most gorgeous college campus in the United States. But after almost 3 weeks of visiting there, I had seen enough to know that I would never want to live there, and if I ever go back to visit I want to go to another island.