The best advice I can give you is to research job prospects keeping in mind that when you talk to the prospective employers, they will not come close to any kind of commitment because you do not live here yet. People are always dreaming about moving to Kona and most often it never happens so, they have heard it before.
At some point you may need to take a leap of faith and just do it.
When my wife and I moved here, I left a good paying, regional manager job at a nationwide mortgage bank and opened a small finance company here. We were nervous and had an abort plan should our bank account reach a certain level. We worked hard, had a few good breaks and never came close to leaving. Good luck with the path you choose.