I dunno, Maui is a more expensive island than Oahu. I lived in Maui and the CHEAPEST place I could find was a room in someone's house way up in Haiku.. it was still $600. (which was way more than 50% of my income from PW!)
You're right.. first year FO pay at Hawaiian sucks too.. but that's not an apples to apples comparision. UPS first year pay is $30/hr, would you say they are on the same boat as PW because their first year pay sucks as much as PW? Hawaiian is a destination airline, and pay DOES get a lot better after that. That's why pilots are willing to put up with crappy first year pay at most majors because they plan to be there for life. As for PW, or other "stepping stone" places like regionals... you have no idea how long you will be "stuck" there with sh!tty pay and shi!tty QOL... that's why a lot of the guys on here tout QOL and pay at the "better" regionals so much. Because when you get stuck at a crappy company for a longer period of time than you planned, you'll realize the importance of decent pay/QOL.
As for your Island Air comparison, that's not apples to apples either. Your $30k is for captains at PW, and you were comparing that to FO pay at Island Air. Like you, most pilots at PW are hired as SICs, and they definitely don't make more than FOs at Island Air. Also, Island Air is multi turbine time which is acceptable to majors, single turbine (non-military) would not be accepted by most majors, if any at all.
And besides the whole pay issue, I just found their managment (or lack thereof) just atrocious. They treated us like we were scum. Maybe it has gotten better for you now, but you have to understand, that the way it was only in the past recent years and that's why they have such a horrible reputation.