Hey Neal, so you thinking about moving to Hawai'i huh? Having been born and raised here on O'ahu, I can tell you that it's a great place to live. There's the year-long sunny weather (it's cooler and rainier from September to about April), good surf on all shores, good food, chronic weed, an eclectic nightlife, a very racially-diverse population, and a burgeoning film community. It's the one island in the chain where you have a strong mix of city and country lifestyles, though all residential areas have urban infrastructures, some more so than others. It's a crowded island (permanent pop.- about 880,000) and the other islands with relatively big populations like Maui, Kaua'i, and the Big Island are definitely less crowded and developed and they may suit you.
What does it take to live here? Money would be a top priority as our consumer prices are a tad more inflated than on the mainland, due to shipping costs. Median single-family homes on O'ahu are in the $620,000 range and rents have also gone up, where a nice two-bedroom can fetch about $1800 and upwards a month. There are a lot of different fields to work in and Hawai'i currently has the nation's lowest unemployment rate, though tourism is the state's number one industry and a good portion of the population works in the various businesses like myself ("Tiki's Grill and Bar" in Waikiki). You also have to get used to the idea that this is the most geographically-isolated place on the planet, so airplane travel costs have to be accounted for if you want to go somewhere.
Like I mentioned before, this is a wonderful place to live with kind, mellow people and a beautiful environment.