What does your son think of all this?
As a parent of children and one who moved around many times when younger, a parent never should ask a child what he/she thinks about a major family decision.
My parents never did. They just said, āweāre movingā and went on about telling about what the new place would be (the positives, etc.)
Parents are there to do the right thing for their kids whenever something big happens. You can ask children about their feelings after the fact and try to help them through something like a big move as best as possible, but donāt get them involved in the decision beforehand. Let parents remain the adults and children remain the children. Iāve had more than enough experience at moving around to understand this topic quite well.
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IMO your best option is to get married (assuming you do love your partner, and expect him to be your lifelong partner; if not, do NOT get married!). After getting married, you can be in Taiwan on a spousal ARC with open work rights for as long as you want. You can work, or you can not work, up to you. This is the visa type I am on (also American, with a Taiwanese spouse), and I just went through the process about 18 months ago so feel free to PM me if you have specific questions. Also, your lack of a 4-year degree wonāt matter if you have a lot of experience and area at management level, with a spousal ARC in hand. What matters at that point is: can you do the work, move the business forward, build successful teams, etc etc.
As for work, yes, you can go the English teacher route, but if you have substantial experience in IT/marketing (e.g. Director level), you may find that you would be valuable to a Taiwanese company or even an MNC operating here in Taiwan. There are absolutely positions out there which donāt require any Mandarin at allā¦ I have one and know others in the same boat. But, itās tricky. You sort of have to get lucky, work your network/connections, or kind of create your own position within your company. People take different tacks and there is no One True Road.
I donāt have kids so canāt advise you on that front, but as others have said, the big international schools are extremely expensive if you are on a local or close to local salary.
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When I was 13 and buckteethed, I got braces. I raged against my parents. āI hate this! How could you? Itās all your fault!!ā blah blah blah, etc.
Now I thinkā¦ thank god they did that for me so Iām not walking around looking like Bugs Bunny. Kids donāt always know whatās best for their development. If they did, weād let them eat candy all day and never attend school.
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As a parent of children and one who moved around many times when younger, a parent never should ask a child what he/she thinks about a major family decision.
My parents never did. They just said, āweāre movingā and went on about telling about what the new place would be (the positives, etc.)
Parents are there to do the right thing for their kids whenever something big happens. You can ask children about their feelings after the fact and try to help them through something like a big move as best as possible, but donāt get them involved in the decision beforehand. Let parents remain the adults and children remain the children. Iāve had more than enough experience at moving around to understand this topic quite well.
Exactly! At his age, every decision we make is going to be bad for him ā from his point of view.
Yes! 
We might indeed end up getting married. Thatās sort of what we are leaning toward at this point.
Another thing that I thought of that I didnāt consider before is that 99.9% of the tasks I do at my current job can be done from anywhere, so itās possible my employer would entertain the idea of allowing me to work from Taiwan. We have a very good relationship, so if/when I am certain we are moving regardless of the job situation, I will bring this up to them. Worst case, I can search for a job once I get there.
And thank you! I might PM you if we need some guidance on the spousal ARC process. 
Over the past couple days, he actually seems to be warming up to the idea a little bit.
He has some cousins in Taiwan and his grandparents who live here in LA with us would move back at the same time.
To do that legally, you basically need to get married. Search for ādigital nomadā threads for more info.
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I would recommend talking with your current employer, my wife and i decided to move to Taiwan as the opportunityās for her are much better than in the uk.
I went about creating opportunityās for myself through contacts i have in Taiwan already and though i would maybe teach a little part time, as i used to do it in other parts of Asia when i was young.
I let my company in the uk know what was happening after my last trip to Taiwan at Christmas. From then on i was working with my uk employer to set up new systems and get people in place to cover me when i left. During my last week of work the CEO and the Design manager decided they didnāt want me to leave the company.
It has taken us one week to negotiate a new contract, sort out all the uk legal issues, work out remote access to the system and set up a work flow that will allow for the time difference. you could easily do this in the 6 month time scale your looking at if your employer is willing.
I will now be working part time from Taiwan, still need to sort out the Taiwan side properly but i would defiantly recommend looking into this option.
To do this i think your only option is to get married. you have your reasons to not want to get married, but it sounds like you have the support of a good family who are willing to move with you. i wouldnāt like to say its a marriage of convenience but what ever your relationship has been for the last 15 years your still speaking and working together for the good of your family. that is much better than a lot of marriages i know.
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Iāve thought about it, but much of the US is the same situation that we face in LA. We have lived in other states in the past. Up until now, all he knows is the USA and he is taking a thuggish direction that we donāt approve of. What we really want is a more Eastern influence so he can get to know his Taiwanese heritage better. I realize that Taiwan is not perfect and that there are bad apples there like there are everywhere, but there are less of them and that type of behavior is not glamorized nearly as much as it is here.
Heās also part Japanese, and living in Taiwan would make visiting relatives in Japan easier, too.
Taiwan isnāt completely uncertain for us since my sonās father and uncle grew up there.
When you get to Taiwan (or even now), perhaps think of enrolling him in some martial arts classes (qi gung, judo, etc). Our children take Taekwondo (yes, Korean, but very popular in Taiwan as some athletes have won medals at various summer Olympics). It helps āstabilizeā them and teaches them to respect the teacher, to always listen, donāt fidget when sitting down in front of teacher, etc.
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Thanks for your input. It reinforces what Iāve been thinking over the past day. Hopefully my employer will be cooperativeā¦
Yes, we would definitely do something like that. He took tae kwon do when he was about 5 years old and Iām sure heād like to try it again. I also want him to continue with the activities heās been doing here: fishing and tennis.
The problems we have with him arenāt related to listening to teachers or doing school assignments, fortunately. He cares very much about his academic performance. The problems we have with him are more like passive-aggressive behind our backs defiance.
Will doā¦ thank you!
So you need to submit 2 reports, one to get a family-based ARC and one to get a job at a buxiban. I did that 7 years ago and did not have to do it again for the APRC. Yet, I am changing jobs and the new employer is telling me I need to get one, have it translated and certified. As I understand it, this has to be done EACH TIME anyone changes schools. Damn. On a bureaucratic level, Taiwan takes the cake!
I wonder what Janet ended up doing. Just to weigh in, getting married opens up all possibilities. The JFRV is so much more valuable than an ARC.
Hope she did it. Howās the kid doing? He should come play hockey with us.
Hello Toe_Save! Sorry for the late response, but the email I got about your response to this thread got pulled into my spam folder.
No, we have not moved to Taiwan yet. Thatās not to say that we never will. If we do, we would most likely get married just to simplify things and open up all possibilities, like you said.
Hereās why we have postponed moving: Considering all the issues we have had with our son, it has been top priority getting those worked out on a fundamental level. Have you heard the saying, āWherever you go, there you areā? Thatās how we feel at this point. We didnāt want to just run off somewhere without resolving the real issues first.
We pulled our son out of the local public high school and put him in an online high school that is state-accredited. Itās mostly online, but he has met his homeroom teacher in person, interacts with all his teachers and classmates via live sessions every day, and periodically does chemistry labs with some classmates at a school in Simi Valley. His behavior and outlook on life seem to have taken a complete 180 since summer.
It seems as though our son is pretty open to moving because heās suggested it a few times when weāve driven or walked by certain weirdness or unacceptable behavior that frequently happens in L.A. I know all cities have their faults, but this city in particular is really starting to lose its mindā¦ There was one incident over the summer that took place in the parking lot of our gym where a guy was doing some kind of ritualistic thing with a snake and charged toward a police officer with a knife, which resulted in him getting shot. This all went down right as we were finishing at the gym and wondering why there were so many cops blocking off the parking lot. Itās incidents like that, that add up and make living here not worth it.
Hereās a news source, so you know Iām not making up this snake story: 
So when are we moving? Soonā¦ hopefully soon. We have to get some financial things in order, which is precisely what weāve been working on the past few weeks. I donāt want to move out of desperation. I want to take our time and do it right.
Thanks for asking how heās doing! I hope all is well for you there!
glad to hear things have improved through the different schooling regime.
(On a side note, was your email acct g m a i l?
That email service has gone to the crapper, sending normal emails to spambox more and more frequently.)
What city are you looking into here in Taiwan to live?
Yes, itās Gmail. It worked this time to alert me about your response, so I guess itās intermittently working?
Originally, we were looking at Hsinchu City or Taichung City, but really what we want is anywhere that is away from the stress of Taipei. We like outdoor activities.