Please keep us updated on your travel! I believe you will be fine with finances as long as you keep track and be flexible with it. Especially when you get older and less able to work. I hope your online business/work will continue to grow.
Did you quit? I assume you are still planning to homeschool your 9 year old? What is your plan for him until college?
Do you mean my son? Or myself? (I am assuming my son).
First off, I am not sure you really need extremely strong reading and writing skills in Mandarin to live in Taiwan. It definitely helps immensely, especially if you want to integrate and get a local job. However, many do quite well in Taiwan with basic to no reading and writing skills in Mandarin. As well, personally I see the entire job market moving away from location dependent jobs. And when it comes to Taiwan, you are better off doing a job online for a non-Taiwanese company anyways - it pays much better and you do not need to deal with the nonsense of Taiwanese office life. When it comes to making friends and social circles - sure. But you can easily find many friends who speak English, too.
As for my son, he has started some lessons. But he is nine. I am not going to push him in this regard, and Covid has taken its toll on every child’s education, even the homeschooled. Everyone is in a funk. I am sure once we get to Taiwan (if that is where we end up), he will have a tutor, and he will pick it up as he does (or doesn’t). I am not really concerned about it. He isn’t exactly academic minded, but he is very smart with money and business ideas. I don’t see him going the university route anyways, he will more likely end up as a small business owner.
People get their knickers in a knot with Mandarin learning. I started studying it around 20 years ago (and still am). However, it wasn’t until I was in Taiwan that things really started to “click”; and that was three years into my learning. My Mandarin is just fine. Patience is needed with everyone right now, and especially with where the world is presently.
I have not resigned yet. We are getting rid of stuff right now (selling/donating). Then we will have to do a few small repairs and paint. After that it will be time to sell the house (probably October). The housing market is crazy here right now, so hopefully it will sell in a week or two (the house next to us sold in one week!). After selling the house, I would put in my notice at the beginning of November; November 19 would be my last day. After that, we hope we can spend Christmas in the house, and hand over possession for the first week of January. Then we fly January 31 to Puerto Vallarta.
As for my son, we have been homeschooling him since last October. It has been pretty good overall, but we definitely have not been pushing him hard during Covid; it has been hard on everyone, and especially kids.