we're more or less in the same boat. My wife is in a field she can telework, I am not as I work for the federal government. I could work in hilo, but that facility is full, honolulu is not. Honolulu pays a lot more, but as you said, the cost of housing is so much higher I think I'm worse off on oahu. Basically my choices are hang here until I can luck into hilo or retire and move to the BI anyway, or take a gamble on getting honolulu and seeing if it's easier to bump over to the BI from there once established a bit. I think yours and my feelings on the BI vs Oahu are pretty much the same. I come from a more rural area and the BI is much more the pace I enjoy. Denver is not.