Cheapest accomodation would probly be one of the backpackers in Paia, get a safeway member card for cheap food, fly hawaiian cheap and easy on excess baggage.
Sleeping in a van is OK if you can find the right spot (away from the crack heads) but this is not recomended as you might get in alot of troubleTheres heaps of cheap cars to buy over there not sure about insurance though. You can get rental cars for as little as 25us a day cant remember the name of the place but its in kahalui someone will know cos heaps of windsurfers use them.
July and august are best for wind but there wont be any waves. Spring or autumn give a good mix.
Getting a job should be alright I worked as a labourer for the stones when I went last year cleaning up rubbish on a building site hard work but good tax free money.Lots of building going on and they were always keen for hardworkers.

You will have heaps of fun so book your flight know!!!!

Not 100% sure. if i go at least 3 to 4 weeks. Do you want to join?

Hee hee hee hee. Me and a whole bunch of guys are leaving for Maui 3 weeks today.
Warm wind and water beats the s**t out of winter in Sydney

Hey Guys
I'll be in Maui from the 15 of July, I'll be available for some demo days so if you want to test drive some new Goya, Quatro or Hot Sails Maui send me an email.
Good wind&waves to all
Ciao
Alberto

I suggest if you are likely to get consistent wind that you take your own gear but be prepared for the excess charge of 100 us each way inter island .Gear hire is about 40 us per day .You can get a damage waiver but it onoly covers you up to 125 and the gear must be repairable.So you pay $4 per day for up to $125 of repairable damage and have to pay an excess of 30 us for any repair even if you have the damage waiver.
I got 50 pc sailing as they say this year is unusual.We did get some waves in May so not all bad.
Al west windsurf van rentals are great.fish market resto at Paia is good for a post windsurf growl.Hookipa is the go but when there is no swell there is really you could sail anywhere.More wind gets in to Hookipa when its SE but when its East the headland gets in the way and it is stronger at Sprecks or Kanaha with the ventury effect.Don't overlook Kihea as this may be the only place you get swell during summer but works mo0re on a northerly to funnel through.
Its expensive but everyone is cool.
Apparently Kanaha can be bad for breakins but I didn't get this impression -never know.

There is an illusive nude euro chick beach but that HOly grail you will have to discover as I never did.Next to Sprecks so the legend goes.
Have fun but if I had my time over I would stay in OZ and go to green island especially in US summer when its flat anyway.Get as much sailing and pay 50 aust for the ferrry apparently.-by the way its pretty choppy most spots .This year has been a strange one but coming into summer for real the trades should settle in .

Hey bakloop - bestflights.com.au just brought out pacific packages - $699 Fiji 5 nights including flights!