Are the benefits of living there enough to offset the hassle?
Depends on what you're into. The outer islands - all of them outside of Oahu and Hawaii - are really one trick ponies when it comes to things to do if you're not a tourist at one of the resorts. Outside stuff - that's about it. If you're the type that really enjoys getting outside every day - beach, mountains, hiking, fishing, outdoor activities and sports - then there is a lot to do. For everything else - it's pretty dead.
Outside of the resorts and tourist traps, there's just not a lot to do commercially. Businesses close early, the locals are clannish, there's limited social entertainment, the road and development infrastructure just isn't there. Maui has more than Kauai, Molokai and Lanai have the least. 90% of Lanai is privately owned. It's very expensive to live on the outer islands and you're limited in what's available - Try buying a car on one!
The Big Island - Hawaii has a couple of larger towns - Hilo and Kona which have pretty much everything a 50K person town on the mainland has commercially, but still, the streets tend to roll up early and there's limited "fun" types of venues. Again, if you're the outdoor type, you'd have plenty to do. The interior of the island is kind of "Wild Wild West" - think fast and loose... Lots of area are virtually "Kapu" - off limits to outsiders. Very little infrastructure or road network and only very small towns outside of the 2 big ones. The whole island which is the size of a New England state only has 250K people living there.
Oahu? It's got a million people and everything you'd find in a major mainland city - along with the worst traffic jams you'll ever see (LA not withstanding) and all the commensurate ills of all big cities. It's the really different culture (very Pan Asian) and attitude (lets just say that urgency in anything is lacking) prevalent there that makes adjusting and fitting in difficult for a lot of mainland transplants (especially the high pressure types). We even have a term for it - "Hawaii Burnout". Folks move there after buying the tropical paradise schtick put out there by the tourism board only to find reality is very different when you actually live there (and expensive).
Just getting a job is difficult for many because employers don't expect you to stay (a year or two is average for most transplants before they give up and go home) and don't want to sink the money into you to train only to see you leave as most do. Having said all that, if you can adjust to the differences and learn to - well - just chill - and reset your clock to "Hawaii Time" and adjust to the island rhythm and flow of life, then it can be a wonderful place to live. I certainly plan on moving back and that's even knowing how things REALLY are there, but then, I'm an Island Boy!
Cheers!