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By the way i'll give you a friendly tip on how to survive here: it's not what you know it's who you know ..... the locals really hate people that come over to work they feel as if we are stealing their jobs. When you go to other island other than Oahu you will find a lot of lazy Haole surfers (especially on Maui) that think the island belongs to them and they will stab you in the back as fast as a drunk would take to a drink bottle - especially if you are another Haole.
I've seen the way those Haole treated real Hawaiian and Japanese with underlying racism. It's really sad to see white people being so racist especially when i am white myself.
So... the whites are especially bad to other whites, and yet they're somehow racist?
OMG I am laughing so hard. $5k will last you about 2 weeks.
Laid back? AWWWW, cute! People hustle with 2 or 3 jobs to pay rent/mortgage/gas.
The last thing KAU needs is more laid back people who sold everything thinking they'll make a go of it on the Garden Isle. You won't be well received.
Haoles vs locals? A tired argument that always ends the same way.
Ah, Ka'u is on the Big Island, not Kauai where the OP is planning on going.
Well, the $5K will last for awhile if he spends it wisely, but there are quite a few upfront costs which will eat huge holes into, that's fer sure. Once he gets settled, though, the weekly expenditures should get lower.
1. A motorbike (perhaps an enduro) sounds like a really good investment to keep things cheaper. The lack of winter makes it more practical, assuming you're not in an extremely rainy area. Hawaii drivers are supposedly a little slower, but are they any more reckless/careless than mainland drivers, or less so?
2. Round-Trip ticket sounds key, just in case.
3. You should be ready to live very simply if you don't want to completely bust your ass. Maybe lots of rice (with some veggies) and water. (I might quit milk entirely if I move there, or just drink powdered milk.)
4. Given the price of rent, some sort of housing investment probably makes sense if you have a few bucks. Maybe go in on an older, larger house with a few other people. Being able to keep your monthly nut low, and also having an asset you could sell if/when you leave, would be nice, as opposed to simply p***ing away your savings on overpriced rent while there.
(If you had like 20 good friends, half of them couples, all willing to invest $20K each in a $400K four-bedroom place, it seems like you could get a pretty nice informal time-share situation going. Since weather is good year-round, the 20 people could share the 4 rooms without stepping on each other's toes too much. Unused rooms could be rented out for certain periods to cover expenses, etc.)
5. Bottom line, if you want a laid-back lifestyle, you'll need to plan out how to invest your money most wisely, and live as cheaply as possible. If you could afford a house where you could also rent out a few rooms, that would probably work well. Otherwise, as noted, $10K, $20K, or even $50K could go pretty quickly.
6. There's so much negativity in many of these threads, it does make you wonder. I'm sure most of the issues noted are real, but you kind of wonder why anyone stays if it's really that bad. Maybe because new transplants mean more job competition, higher prices, etc? Or just frustration with high costs and low wages, despite a love for the surroundings?
But as goofy as the thread title sounds, as long as the OP has a return ticket, and a few bucks, it doesn't really seem that crazy to check it out and see if he likes it. Just as long as he knows how most people live. WOOF might be a good option for him, or others in similar situations.
Quick update on whats been going on, never made it out of the USA
1. Sudden death in family, moved ~4 hours away to take care of relatives for about 6 months
2. just moved back and working in a large engineering firm, directly under the president in business relations and business development.
Still have the itch to get out there, most likely going to take a ~7 day vacation in about 3+ months just to visit and tour, still job hunting if anyone has any connections or leads.
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You spend $2500 a week? 
Wowsers, I know Hawaii is expensive but $5000 for two weeks? 
Update****
