Hawaii has been and still is the dream of tons of people on the Mainland, more so the ones going through the rough winters like the Canadians. No wonder that the 'snowbirds' from Canada and the Pacific Northwest show up each winter in Hawaii for the simple reason that they want to see some sun!!!
And each time the snowbirds are here in Hawaii, they are wondering what it would be like to live in Hawaii for good. For the majority of people, the biggest question to contemplate is finding a job in Hawaii. Employment in Hawaii is the basis to sustain your and your family's life, whether being on the Mainland or in Hawaii.
Finding a job in Hawaii, provided you have to work in Hawaii because you are not independently wealthy does not come easy. If you were extremely lucky as a college teacher, you might get a job at the University of Hawaii. I would not count on that. Those who have a good teaching position there or at a nice private school like HPA Hawaii Preparatory Academy or Parker School on the Big Island, don't move too often.
If you really want to live in Hawaii for a longer period, you might want to look into employment at the hotels where jobs become available on a more frequent basis. You might get turned down as 'overqualified' but it's a chance to get a job in Hawaii. Lots of people sacrifice well-paid jobs from the Mainland in order to live in Paradise. However, don't move to Hawaii with all your stuff and kids before you secured your employment in Hawaii. Be aware that hotel jobs in Hawaii depend on the tourism industry. No Hawaii visitors, no jobs!
Quite a number of people who move to the islands get their Hawaii real estate license. Hawaii will always stay a dream destination for vacation or retirees! The more hands-on people get their license as an LMT, licensed massage therapist in the state of Hawaii. It implies to spend quite a bit of money for attending one of the Hawaii massage schools for getting trained, doing many hours of supervised free massages before being allowed to the Hawaii state exam for LMTs.