Maybe you've been dreaming about this place but trust us, it's going to become a nightmare, fast, for you. Maybe just come out for a vacation and have fun without the worries of actually trying to make it work. We could be wrong but based on our lifetime of living here, it's nearly certain to not work out. Still, there are always exceptions so if you're willing to do whatever it takes, go for it!
Sorry but it just doesn't look good for you here and it would be a really big risk. If you're still smitten, though, perhaps set yourself up to take a really long vacation. If you can stand living here for 90 days, then it could work out, but we would bet against it. Still, it's your money and your life so if the spirit grabs you, follow it!
Yours is the tough one because really, it could go either way. You might come out here and just love it, or you could come out here and quickly realize you've made a big mistake. Tell your friends you're going on a long vacation. Stay here for 30 days and if it feels right, tell everyone you're not coming back and start livin' the dream!
You could be one of those rare people that will make it in Hawaii. We're not giving you our strongest recommendation but we don't see too many red flags. If you've been dreaming about Hawaii and are willing to do whatever it takes to make it here, it could work for you.