I can't speak to your question because I'm on the outside looking in. (Logic suggests I should keep my mouth shut). However, I did fly for Caravan connecting flight operation in HI for two years. I lived on a salary of 19,200/yr. Kamaka air is cool local cargo operation out of HNL that doesn't pay well, but it may translate into a check out in DC-3. Island Air traditionally has been slow to hire as attrition from the top is low. Mokulele Air might hire you to fly Caravans right seat if you're interested in building time, but again they don't pay well. I guess just PM me if you get a slot and want a reference for one of those operations.
Edit: But I remember watching the mighty Eagles do an overhead break from the ramp (before they got 22s) and thinking Holy $hit that's fuggin awesome. SO, I'm trying to get a slot there in any equipment, as well.