Usually, when I travel, when I find places I like, I usually think to myself "Hmm, I could live here." I tend to like cosmopolitan cities especially, like Vancouver, London, some German towns.
Then there's Hawaii. Whenever I go to Hawaii, I go through this phase where I think: "WTF is wrong with my life?! Who the fuck corrupted my thinking and told me I gotta work and contribute to society, and all that bullshit, when I could be HERE?! Fuck you all, I'm moving HERE." It usually wears off by day 5.
Once realism sets in, I do tend to think that Hawaii would be a good 2nd home, but it wouldn't be so grand as a place to set anchor, for me personally. I know a couple, one guy born and raised in Hawaii, and a my friend who grew up in CA. They married and moved to Hawaii (return trip for the groom), and so I have the benefit of their perspective.
Island fever is an issue. The drudgery of real life responsibilities seems to follow you wherever you go. My friend said that after moving in and all that, it took about 3 months before she could even begin to enjoy Hawaii, and that she only goes to the beach like once or twice a month.
Food in Hawaii was a real hit or miss with me. Whenever I went to restaurants, it was kinda meh. Fish taco stands and surfer joints were fun, but the food wasn't incredible. The street food was *amazing*. Saimin was great. On North Shore Oahu, we went to this grilled shrimp stand that was phenomenal. I do think that if I lived in Hawaii, I'd end up missing mainland food, mostly due to its variety.
I suppose that's my guarded optimism. Incidentally, I have a coworker who is kind of a beach travel nut. He's been lots of places, Kho Phi Phi, Mexico, the Caribbean (Turks & Caicos), Tahiti, and he says that by far, Hawaii is his favorite