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I say live your dreams if you can. I did. I have been living on Maui for the past 25 yrs. Wife works as a RN/case mgr at our only hospital. I have worked for the Hawaii Dept of Education for 22yrs from teaching in the classroom at all different levels to District Administrative positions. I have two kids ages 7 and 12.  I flip houses for extra income and now own 3 income producing properties here.

Given your information I would recommend you try and follow your dream as you only get one shot at life so why not make the best of it. There is opportunity for your wife to work in the hospital as they need nurses right now. Her pay alone would buy you some time explore your own opportunities with RE providing you budget well. You will definitely want reserve funds to cushion the move so plan accordingly. The public school system is like most others, some good schools some not so good. Some good teachers, some bad. More important is your support and guidance through their school experience. With good parent support they should do fine. Both of my kids are in public school and they are doing well. In many ways public education is what you make of it. If you are engaged with your children and willing to supplement their learning with alternative educational resources if needed then you should be fine.

The rental market on Maui is through the roof strong so consider purchasing investment income properties if you are in the position to do so.
It may take you a while to get cultured to our systems and attitudes so the more humble and understanding you are the better. We locals like humble.
Plan well, live the dream, but have a backup plan in case things are not what you expected.
Hope this helps.

My observation from watching Malibu on the web cam is that basic surfing etiquette is thrown out and its a bit of a free for all regardless of the size. On one of the days from the surf generated by this Hurricane there was nearly 200 out in the water with everyone dropping in on everyone. Just seems to be the way it is at that break.  No offense So Cal folks, but really glad I live in Maui after watching that circus in the water. 

Just wondering if the women who sup in surf ever get the stink eye or run into problems in the line-up??

6 times OH at Jaws ........................in my minds eye!! Triple at Pier One Maui actual.

I remember windsurfing uppers on those really really big days. The current is crazy with lots of water moving around. One year the swell was so big that there was no channel between uppers and lowers to get out through making your timing critical. If you have ever seen the picture of Naish out windsurfing at log cabins called men who ride mountains, you will get an idea of what a really big day at uppers can be like on the outside.  Such a rush to experience!!  The outside wave is like a mountain sometimes triple mast high which you can get a few turns on before racing toward shore to catch the smaller reform mast high which is hollow and fast.  One of my favorite places to windsurf when it gets really big and there is enough wind. Sup on a really big day at uppers is a whole different animal. Hard if not impossible to catch the outside mountain of water but for those with the balls and skills, the inside can be epic. 

To answer the question why a Prius, those around me that I know who have one purchased it soley for the savings on gas and to their pocket book as a result.

This is the method I use which I have found to be the best even in DOH+ surf. I jump into the water behind my board and put my hand directly on the back of the tail gripping the edge of the board. Just as the wave gets to me I push down on the tail while also pushing forward and up on the board. At the same time I duck under the wave with my one arm being the only thing above water, this tightens the lease somewhat which keeps the board from flying out of control. What I am doing is basically the same thing as standing on the board and shooting it over the wave but I feel I have much more control. You will get little to no pull or stress on your leash, your board will usually end up very close when you surface, your board will not be flying in the air, and you will make others in the lineup happy. I have used this technique for a long time and had many comment to me on how well it seems to work. The only drawback is you will need to be able to deal with your body taking some turns in the bigger surf since you really can't do this and dive down deep. DISCLAIMER!! In the really really big stuff like 20ft+ faces you are pretty much at the mercy of the wave so no techinque is full proof.

Looks like he is on a 10'6 gun. Right tool for the job.

There is a saying among surfers that if you are worried about sharks then you probably should pick a different sport. With that in mind, I will say that in the last year my heart pounds much quicker when I break a leash and have to swim than it has over the past 20 years on Maui. I use to windsurf and even surf on a full moon night but would not even consider it now. Losing my equipment on a big day and having to take a long swim to shore was never much of a concern. Now it is.  I am very aware of the stats as PB pointed out. Will this ease my tension, NO. Will it effect my choice to continue SUP, no. Will I be less likely to throw the ball far into the ocean for my dog to chase, yes. Will I have more reservation about where, when and how my children use the ocean, yes. Sad but true, the recent events have altered my judgement to some degree, warranted or not. When there is a terrorist attack on a plane or at the airport, do you have reservations about flying, probably because it is human nature. Hopefully the frequency of these attacks will decrease significantly to help ease the stress and concern many are feeling. I am also concerned about the effect it may have on Maui's tourism.

Body was not found and search was called off after two days. At least he went out doing what he loved.

Yep. I also was at Sprecks Maui one day when Laird was sailing a 5.0 in 40 knots during a photo session. He hit a ramp and went so high in the air that the helicopter had to move out of his way. It was a sight to behold. Bew everyones mind on the beach.  He would chop hop down 25' faces at Hookipa like it was nothing. He did a few Island crossings during his windsurfing days.

You are correct I have no diving background. However, I used silicone ear plugs for 2 mths after I ruptured my drum while surfing  and had no problems. I got worked plenty in those 2 months without any issues.  My Doctor recommended I use them to protect the drum if I was insisting on going in the surf while the drum was healing.
Perhaps in big surf with a deep water hold down it would be a different story. I can say that breaking my drum was absolutley the most terrifying water experience, I am very lucky to be alive after my ordeal. It is a situation which many surfers don't really think about until it happens to them. I would imagine a good way to prevent it is to wear a helmet that covers the ears. 

Pretty sure he broke his ear drum which led to his dis-orientation and drowning. Makes me want to wear ear plugs next time I am in the big stuff. RIP Brother.

I agree that JP is perhaps the best wave sailor on the planet. Been wave sailing myself on Maui for over 25 yrs and I can attest that JP attacks big surf unlike anybody else. I have seen him on big days at Hookipa hitting the lip so late and recovering that it simply blows your mind. Love the vintage footage of Craig M, Dave C, and Doug H, in early competition. Robby Naish dominated for so long in the main events.  Those were the days!! I also remember a day at Hookipa in the late 80's where Craig and Fred Haywood ventured out in 30+ feet Hawaiian. Nothing but massive closeouts and no working channel. Just crazy! They did get some rides but also paid their dues. I think Craig was a rock star that day meaning he spent some pretty serious time getting washed up on the rocks just trying to make it out. Windsurf Magazine actually had some epic photos of that day.  

The jetty side right can be a really challenging section for a sup as it is a wave which pitches up fast and gets pretty hollow especially when head high or bigger. A small sup is the ticket as it fits into the wave a bit better. Most SUP prefer the middle break which has a left and right. I have been out on days where it is well over head and barely makeable on an sup. Very very tough technical conditions for a SUP, great for a short board surfer.  As was mentioned earlier, the harbor is many times the only place rideable as it is victory at sea or too windy everywhere else, hence the crowds.