My main concern about moving to Hawaii is finding a place to rent/live. Also, I understand that the cost of living is higher on the islands than it is here, in Oregon, but I don't really have a frame of reference. We would be living as modestly as possible, at least while we get settled. I guess my main questions for you would be: how much money do you think would be appropriate to have saved up before we move and how hard is it to find a rental. I think we would be looking at Oahu, since there's more business there... but I don't really know! I just really want to live in Hawaii! Thanks for your time."
We know how you feel about just wanting to live in Hawaii. Vivienne and I first visited Maui about 10 years ago and as we were leaving Vivienne said she wanted to live here some day. We visited each island and tried to imagine actually living there. We finally ended up on the Big Island near Hilo primarily because it was most affordable. Fortunately we also fell in love with the place so we've been very happy here.
Each island is different. I don't know which islands you've visited but before you make the big move you should visit each island and see which feels the best for you. It's true Oahu has the most jobs, but it is also the most expensive, housing-wise, both buying and renting. And I hear they have wicked rush hour traffic. Visit the online versions of the local papers and check out Houses to Rent and the Help Wanted sections. Oahu has The Star Bulletin. Locally we have the Hawaii Tribune-Herald.
It probably wouldn't be very hard to find a rental. My main concern would be employment. If you or your boyfriend could find a job before you move out, that would be ideal. Check the Help Wanted ads and start sending out your resumes.