So many questions... moving to Hawaii

First... about myself (so you know who you are replying to!

- I work in an inner city school teaching "at risk" children. I truley love my job... favorite part: beautiful diverse classroom (five languages in one room)
- I graduated college in 2006
- I moved around ALOT as a child (always the new kid, never really minded it)
- Moving with a friend of mine
- I have done a lot of research on HI
- We both pay close to $700 a month on rent alone... very used to living on a budget.
- You may find us at a bar maybe once a month... at the MOST (we are more happy hanging out with friends outside, enoying the sun and nature!!)
-if you were going to categorize us ... free loving, social, nature, funny, hippies would fit pretty well.
Now, questions....
1. Does anyone know ANYTHING at all about the proces of finding a taching job in HI? I know that the DOE hires. I know about furlough and budget cuts. I know about private schools.
-What are the possiblities of scoring a job BEFORE I move?
- Any specific schools/areas to work in ... then live in?
-More likely to find a rural job... what type of transportation would you suggest?

2. Where to live? We REALLY want to move to Maui but have been getting a great deal of Oahu first... advice. What do you think? Where would we fit in in Oahu? We are VERY social. Gone to 8 islands and have made friends w the locals at all of them.

3. Latstly, we both have cars probably around 3-5,000 each. should we drive then ship them? or buy one there? Bikes OK? Buses OK? how long can we go without a vehicle? \

any other advice I am missing would be much appreciated. Anything shocking to fellow movers?

Mahalo in advance for the advice!