It's very simple. Look for a Magnum PI type of situation and you'll be set in Hawaii. If you want to live in a sweet guest house (for free), drive a Ferrari, hang out with Rick and TC at the beech and solve a few crimes here and there, I am sure you could make it work. Probably too many young people on these boards unfamiliar with the good-ole Magnum TV show...
Personally, I'd jump at a 2-3 year "vacation" in Hawaii for Allegiant and then bid back to my normal base later. If you can swing it with your family, why not do it? Do you think you would ever have that opportunity to live in paradise again? Sure, it is expensive but it would be a great life experience for all involved. I thought I had heard that Allegiant mgmt was considering a COLA for Hawaii-based pilots? I could be wrong...
Plus, do you want to fly the MD80s for your entire Allegiant career? I am sure they are fine but I'd appreciate some 757 time (at a "reasonable" wage for the type, please - not sure that mgmt would agree) as well. Some people couldn't care less about what they fly - I am not that jaded YET... Let's hope the wages get some upward pressure as well as new, bigger types are added.