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The proposed plan is doable, but there are some major roadblocks. Yes, 100K income from remote work (with savings and seemingly debt-free) makes living in Hawaii possible, but that doesn't mean it works for everyone. However, with 4 kids you are at the limit where you need to be worried (bigger food budget, bigger car, more activities, etc.). Visiting and getting feel for the neighborhoods is a must. Planning the pets takes time and effort. Homeschooled kids need to take the standardized tests at several key points (can't remember which grades) so they do need to be ready for those. Not already mentioned is the isolation--at that income and family size, your travel budget is very limited. You will probably be able to afford a single family trip to the US mainland once a year. That does not bode well for someone who seems to thrive on international contacts.
As for the minimalism and whtviper1's reaction, several things make me side with whtviper1. Minimalism is good, and I actually disagree with his point that it will destroy the BI economy. Honolulu operates at a higher level, but the BI could still use a few 100K minimalists with out-of-state income. I think that whtviper1 is reacting to the people who come over with 10K in savings and then want to get a minimum wage or state teaching job to survive.
But whtviper1 is correct that "minimalist" is 95% of the time a synonym for "dreamer," and his research into the OP's previous inquiries and role models shows that she leans towards "dreamer." Personally, I do not know any true minimalists who follow mainstream media (those 2 things are practically opposites). Not to put down the OP or any "dreamer," but it's a very long way from dreaming to researching and even further to moving to Hawaii.
If you go over to the Island you like, and spend a month there, you may get a more sobering answer to your plan. I hope you have been vacationing there over the years - first !
Love your tour around the island OpenD, typos or not! I hope you save it and repost it over and over every time a new person comes on the forum asking the same questions about where to live. Especially those who have never set foot in Hawaii!
I am driving along Hwy 11 some warm evening with the windows open and luxurating in the warm tropical night. Low and behold, the gentle fragrance of Pikaki eases in the car and I love living on these Islands. It is so easy to make money as it falls off the trees and all you have to do is pick up what you need and take it to the bank.
Thanks OpenD for the information I asked for. I will do due diligence in covering as many bases from the mainland as possible. The thoughtfulness and work you put into this post is nothing short of kind and I gave you as many reputation points as the system allowed - I wish I could give more for the work you put into this.
While I own the label "dreamer" without shame I can tell you guys that we have researched California and Seattle both only to not act on a move after discovering things that weren't going to work for us. I don't know what kind of mental image people here have formed of me, but let me just say that if you stood in line with me at a Starbucks I would not appear any different from any other mother of four. No tattoos, no piercings, no extreme clothing choices - not that any of those things are bad, mind you.
As far as not being tuned in to mainstream media, well, I am a journalist by trade and was a staff writer for a newspaper in Washington, D.C. straight out of college - hence the heavy travel twenty years ago. I was raised to travel abroad from birth as my Father was a retired U.S. Naval pilot that could never shake the lure of new faces and places. I have interviewed famous musicians to seedy politicians and slept rolled up in corners of too many international airports to count - so yeah, I am a "dreamer" but also a hardcore realist.
I am taking all that is posted here to heart - there is a lot of truth behind the added financial stress of doing this move as a family of six with three pets. The biggest roadblock I have found is the finding a decent rental to accept pets. However, OpenD sent such great, detailed neighborhood info that I will continue to look for the right place.
We have a great deal stashed away in savings and carry no debt but we will try to establish as close to a realistic budget as we can without living there. Living in Asheville is not cheap either - my husband just clarified that we spend $400 a week for groceries whereas I had initially thought it was closer to $300. Either way, I assume our grocery bill will be way higher upon moving without a Costco to hit up for produce.
Comments about the BI not needing incoming minimalists is simply ridiculous - an economy doesn't only grow from people shopping for things they don't need. If that were true America would always be doing swimmingly as frivolous shopping is practically a value for the average U.S. mainlander. The only reason I brought up minimalism to begin with was to make it clear that we would not have the high rent problem that most large families face when needing a large home. We choose to live with less for many reasons but clearly it is not a lifestyle embraced by everyone and that is perfectly fine by me.
Having productive and respectful residents that don't further the drug problem or drain funds in the form of needing welfare assistance is a good thing, right? We spend our money on activities, good roasted coffee and organic produce so clearly many will profit from our existence if we manage to make this move happen. And clearly, we will pay for gas, utilities and internet just as everyone else does.
We have planned a four week trip in November, and the worst thing that could happen is we enjoy a month long holiday checking out a beautiful island. If it works out we will be happy and if it doesn't we will still be happy.
To the posters who raised concern over grade level testing - my 16 year old twins tested out of 12th grade with flying colors four years ago. That's right, 12 year old kids that have never seen a day in American school tested four years ahead of their peers. My kids are pretty bright but this is not an unusual occurrence for unschooled kids - they tend to tear through subjects like science and math early on and with very little prodding. I never said they didn't have access to Algebra and Trig textbooks and even a math tutor at different times over the years - unschooling is simply that, no set study times, no set subjects and no set sleep schedule - but when they choose to dive in to a given subject I make sure they have everything needed to succeed.
As for the minimalism and whtviper1's reaction, several things make me side with whtviper1. Minimalism is good, and I actually disagree with his point that it will destroy the BI economy. Honolulu operates at a higher level, but the BI could still use a few 100K minimalists with out-of-state income. I think that whtviper1 is reacting to the people who come over with 10K in savings and then want to get a minimum wage or state teaching job to survive.
But whtviper1 is correct that "minimalist" is 95% of the time a synonym for "dreamer," and his research into the OP's previous inquiries and role models shows that she leans towards "dreamer." Personally, I do not know any true minimalists who follow mainstream media (those 2 things are practically opposites). Not to put down the OP or any "dreamer," but it's a very long way from dreaming to researching and even further to moving to Hawaii.
I'm for the OP on her move, no doubt. 100K/year from outside of Hawaii, that's basically money going directly into Hawaii and coming from somewhere else.
Regarding the 'minimalist'. I'd have to agree with common sentiment on here. In my opinion, 'Minimalism' works great if you're a priest, a bachelor, or just a young wanderlust. I've never heard of a Family of 6 living the minimalist dream, unless they were classified into poverty. Kids just aren't geared that way. The celebrity referencing as minimalist examples showed a further disconnect. But, in my opinion, high income earners generally have a huge disconnect with their own reality anyways. So, I'd certainly overlook that.
Despite the 'dreamer' side, and the 'disconnect on minimalism'....I think she could definitely make it on the Big Island of Hawaii. Asheville people and Big Island people are somewhat similar types in many ways as well. I think her kids will definitely have an educational experience with a Hawaii move, and they certainly have the income to bounce back to wherever else, once they actually saw if it was for them or not. Maybe it would out just fine for them as well.
Not only that, but I wouldn't mind seeing continuing posts from the OP as she lives out a dream on the Big Island, and her income would warrant it having a decent shot. In my opinion, the only reason she wouldn't 'make it in Hawaii', would be that she might dream up another life scenario a few years later if she was living on the Big Island. But, if so, so be it...
Thanks for sharing your take on things. But if you go back to my original post I made it crystal clear that we had secured a liveable income and would not be a financial burden to the local economy. Please reread my OP and Viper's kneejerk response - he came across with anger straight out of the gate. I was advised by several on this forum to block him as he is a known bully with "problems" and as of today I have done so.
Mod cut: off topic
As far as minimalism working with kids - they have everything that they love and need but nothing else. My teens each have a lap top and I pod but only have maybe a dozen items of clothing and a couple pairs of shoes. My eldest son also owns an electric guitar and art supplies as these are his interests. My eldest daughter has a hair dryer, but only two pairs of jeans and this is because she doesn't have a need for more - if she did we would not hesitate to buy her more.
We are still hoping to give Hawaii a go as I believe the overall experience would be worth the money spent. As for me dreaming up a new scenario a few years down the road - expect it! A few years in Australia would probably be a natural follow up to Hawaii - minimalism lends to easy movement after all. A nomadic lifestyle must seem strange to many but it has definitely served my family well - and for the record, we run any and all plans past our kids - strange again I am sure but different strokes for different folks.
I am not trying to shove my belief in minimalism down anyone's throat but put this info out for anyone who might be truly interested. So much hardship comes to families through debt caused by assuming having kids means spending a small fortune on stuff and I want to spread the word that while ours is an unconventional approach there is no lack of joy or abundance when you pass on the mass produced crap that is pushed on every new parent. Nor am I passing judgement on those who have full closets of designer jeans - it is just not for us.
While I have read this entire thread, I'll not comment on the responses so far except to say that you've received the traditional "welcome" from all the regular posters... I think you can really call yourself a C-D member now!
Our family moved to Kona at the end of February. We have one preschool age kiddo. Our move was not ideal in some ways that I will detail below but I know for sure we did some things very right and I'm happy to share my experience in the hopes that it will help you plan and decide if moving here will really be the right thing for your family.
We had come to the BI on vacation multiple times and in 2011, we booked a new-to-the-market vacation rental for 3 months to try out living here. (We were lucky to find this rental, they had literally just listed it on VRBO as the new owners). This is what I recommend for everyone... spend as much time as you can afford on this "tryout". But AT LEAST a month. You need to be living, your hubby needs to be working, the kids need to be doing all the things they do. You need enough time to get over the sun and the beach and all the tourist stuff and settle into daily life without stars in your eyes. I'm not sure a month is really enough, but it's a good start. You need to be shopping, cooking, filling up your free time, and all the rest of the stuff you don't do when you're on vacation.
Even with this extended tryout time, living here is another thing entirely. We have found that literally everything about how we order our lives has had to change, from cooking (who wants to cook dinner and heat up the house during the hottest part of the day? Not me. And some of our favorite things to eat back in WA no longer appeal here.), to getting around (Kona has limited roads and a lot of people; traffic is an issue, especially January-March and during rush hour times), to filling up a house with furniture and necessities (even second hand stuff is MUCH more expensive here, and people try to sell stuff that should be at the dump).
Building relationships is difficult because so, so, so many people move here and leave. I've heard that 1 year is sort of a magic turning point. We are part of a wonderful church, and that helps us a great deal, but even there... building relationships is not happening as it did in other moves. People are very friendly but not necessarily jumping up to invite you into their social circles! We have lived on both coasts and I lived overseas in college, so we are well versed at moving and not expecting things to be the same as where we grew up. We have lived in small towns and big, diverse cities. Hawaii is nothing like them! It's really its own, very unique place.
We do meet people everywhere, my daughter has no problem playing with other kids on the beach, at the playground. We meet tourists, locals, transplants. Everyone has treated us with kindness. We do our best to be respectful and acknowledge that we are guests and to just sort of... blend and go with the flow of the island. Even so, we are pretty much taken for tourists most of the time. I suppose it will take quite a while for me not to just carry myself like a mainlander! I'm just fine with that. I'm grateful to live here.
We are in a quite parallel situation to yours. My husband is an independent software developer with a long-term contract back on the mainland, and I'm a SAHM who plans to homeschool. On that note, look into Hawaii's regs on homeschooling of all kinds. I know you are unschoolers -- here, your kids won't get a diploma. They will have to take an adult GED course of some kind when the time comes. Unless, with your older ones, you could take care of some of that before you move.
While you're here, drive all around the island. It's shocking how diverse it is! We like Kona and the sun after living in the pacific northwest for 10 years, but Kona is busy and crowded and touristy. But we think Waimea is just an amazing place and it couldn't be more different. We'd be sorely tempted to live up there if our church wasn't here. Captain Cook has its own charm and so many people love the lushness of the east side (we are unhappy in too much humidity, so Hilo isn't for us). Although there is so much going on in Hilo that sometimes I'm tempted! If you can stay a couple weeks in a few different areas, that would be an awesome experience.
I think someone mentioned once you move, commit for a year as a trial -- that's exactly the advice we were given and exactly what we're doing. If I had it to do over, I would have rented a furnished vacation rental for a month (or two places, two weeks each, whatever I could arrange). Immediately rent a storage space, start thrifting and stalking Craigslist for what you need. It will take that month to be able to find things you like at a reasonable price. I had to settle for some less than ideal furniture because I didn't do this. We spent a few days in a hotel and then another couple of weeks at a bed and breakfast and spent that time only looking for our long-term rental -- not shopping for stuff. I would have given us a month to find a long-term rental AND thrift shop.
Why the year thing? What I said above is true, literally everything about life here is different (except, perhaps, shopping at Costco, though even that is uniquely Hawaiian). You just have to see, long term, if living on a very rural island in the middle of the pacific, in a polynesian culture, is a good fit. You have to find out if you are as adaptable as you would like yourself to be. Most people aren't, and that's not being harsh. It simply means we like what we like, and don't often realize how much we are tied to a certain way of life, certain ways of doing things, certain ways the world works, until we are taken out of them -- even by choice.
And, about the pets, I'm going to be brutally honest. DON'T BRING THEM. I know they are a part of your family. I KNOW. We said goodbye to our dog of 11 years to a good family friend when we decided to move to Hawaii. A friend of mine here, who moved with three kids and two dogs... they had three months in a vacation rental to look for long term housing and about 98% of rentals on the market won't even consider pets. They were very, very stressed out. Finally they got someone to rent to them, but are paying much more than they wanted to pay for a smaller place. And it took literally WEEKS for this landlord to decide to rent to them. (Weeks of hoping this ONE house they found, in the school district they wanted, would rent to them.) I would NEVER bring pets here unless you plan to simply buy a place outright. I also wouldn't have put my dog through the flight and transfer that needed to happen to get him here, it wouldn't have been a good thing for him. It's hard enough to find a good rental for a larger family... throw in pets and you have a recipe for stress and stress, and more stress. Plus the vacation rental for the beginning of your stay has to let you have pets, too! My friend admitted to me she thought the "don't bring pets thing" was overblown and that when people met them, met their family, saw how well-behaved their dogs are, it would all work out and be OK. She found that not to be the case. At all.
We brought our cars, it was an excellent decision. I'm not sure it would be as cost effective from the east coast, but there aren't a lot of cars here to choose from and the used ones aren't in good shape. Again, I have a friend who settled for less than they wanted simply to get out of a rental car. If we don't end up staying in Hawaii, we will sell them for much more than we could on the mainland, they are both 4WD in excellent condition, make a profit, and find something else back there.
In my opinion, you have a lifestyle and life experience that would serve you well if you decided to move here. I'd be bummed if you chose Hilo, though, because I think we'd get along really well!
We are at the 3 1/2 month mark in our year trial. At this point, we are undecided about staying long term. I think we probably lean slightly toward going back to the mainland, but that may be only because we are in that transition place of not yet having a deep social network -- not because of anything about living in Hawaii per se. We love so much about being here and our feelings and experiences will change over the next 9 months, for sure! My very favorite thing about living here? Going to the beach at about 4pm, when everyone goes home for dinner, and bringing a picnic. Playing with my daughter in the waves and watching the sun go down. In the pacific NW, 3/4 of the year it's dark and wet and not very much fun to be outside from 4-7pm, and hard to entertain an active little one. Now it's my very favorite time of day. Early morning is awesome too. I'm not much for the heat of midday, but I wasn't much for the cold pacific NW rain, either.
My least favorite part? Centipedes. Hands down. Hate them, will always hate them. Spiders and cockroaches don't really bug me, but centipedes? Mean little dudes (<-- insert your favorite choice word here).
I moved to Kona ten years ago with wife and a few kids and plenty of money in the bank. It took 5 intense, expensive years to get the business a tad profitable and we are doing OK now. I met quite a few similar folks but none of them makes money and the average time they burn through their savings and leave again is 2-4 years.
Best thing for you to ponder is a decent exit strategy in case things don't go your way. If gives you a calmer, more rational approach to the whole endeavor.
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I think you can really call yourself a C-D member now! 
