With your spirit and desire to live in Hawaii, I am sure that one day it will happen.
The most challenging part of your scenario will be finding a job. Hawaii is very tourist dependent. While Hilo is less dependent on tourism, because of the economy, jobs are hard to come by. I would recommend that you apply for jobs before you make your move, that way if you are hired, you will have a better idea where to live so that you are close to work. There will be more jobs on Oahu, but the cost of living is much higher.
If you plan to save up money to live on while you look for a job, estimate $600/month for rent (although you should look at the local papers to get an idea how much rent is: $100/month utilities, $300/month food. If you live in Hilo, you can get around by bus. So if you live frugally you could probably get by on $1000/month, just for the basics.
When you're ready to move, contact a property manager at a real estate office to help you find a place to live. They can help you get settled and make you r transition much easier. My property manager is Tammy Medeiros at Clark Realty Property Management and she is really nice.
It will be tough making the move and not knowing anyone. You won't have that support network of family and friends when you get there, so join a church or a canoe club and try to establish friendships as soon as you can. Maybe take some classes at the community college.
My last piece of advice is to take more money than you think you will need, because everything moves much slower in Hawaii (and costs more). Also, checkout the PunaWeb forum. They are happy to answer your questions, too.