Hawaiian is hands down my first choice for my career. I am doing all I can professionally to build my qualifications as a pilot - currently a regional Captain, but I want to figure out how to stand out otherwise. I figure buying a 'cheap' condo might help show how serious I am. If for some reason HAL doesn't call, I still travel to the islands often and a place to stay / airbnb out isn't a bad deal for me. I have spent fourteen of the last fifteen years in the SF bay, and what I can get for a dollar on the islands is better than anything in the bay, so if I'm going to invest in property, might as well be Hawaii. COL is technically lower (by 1 whole percent).

Thoughts? Better ways to stand out?

I had considered getting a job flying the Dash at one of the Island private dash operators, but was told sticking where I am now is the better choice.