wow I cannot believe it's been nearly 4 years since my last post and visit to this site! I've just caught up on my original thread as well as this new one. I'll update you all on our past 4 years.
In April of 2021 I was awarded the Taiwan Gold Card and we were able to make our plans, finally knowing we had an easy path to live in Taiwan. At the end of 2021 we moved out of our Miami home and began our nomadic journey, primarily through Puerto Rico, Mexico, Texas and California. About 9 months in total, but did not manage to learn more than rudimentary Spanish

Our kids were 6 & 4 that year. Then in August of 2022 we officially relocated to Taipei. My older son immediately began 1st grade in the local school system and my younger son started the equivalent of Pre-K at a private kindergarten.
We're now very settled in Taipei, love our life, love our school (boys are now in 3rd and 1st grades at the same elementary school) and we've gotten back into business after organically finding a business we're passionate about and also seems to be very lucrative. I say
seems since we're relatively early in the journey, but all things seem great so far. I'm also pursuing my music career pretty seriously now, and I'm finding things working out as well as I could hope, though perhaps a tad bit slow.
Being based in Taipei but with kids in school full time has meant we only travel during school holidays. Nevertheless it's afforded us family trips to Indonesia, Cambodia, Thailand, Philippines, Hong Kong, Macau, China, England, Vietnam twice, Singapore twice, Japan twice, and Malaysia many times (I have family there and now business too). We've also been back to the US once each year, which will continue with a long trip back this summer (plus a first time to Peru!!)
We plan to stay another 2-3 years but it's possible we'll stay longer. The two major factors causing us to prepare to leave are my parents' health (they live in north FL) and the rigorous school system that likely reaches unbearable levels in middle school. The outlook at the moment for when that time comes is:
1) LA - I think this one is 36% likely. We have lots of friends and family there and the weather is generally great (current crises notwithstanding). I think it's likely my parents would join us AND be happy living there. Cost is a concern but we're projecting to do pretty well and for a temporary stay (6-8 years) it should be manageable for us.
2) SF - 35%. Basically neck-and-neck with LA but I put the former slightly ahead. It's my wife's favorite city in the US, her brother is planting roots there with his family, and we also have plenty of other friends and family in the area. Same cons as LA, except not sure if my parents would join us and also weather not quite as preferable.
3) Vancouver - 20%. This one is kind of a wild card. We both really like visiting the city, and we both have lots of family there. My parents were the only ones among their 13 total siblings to move to the US..most of the others moved to Vancouver. Basically the same for my father-in-law. So my kids would have lots of second cousins. Downsides, in addition to cost somewhat, are weather and needing to navigate the immigration system again. I'd strongly consider the self-employed in the arts visa if Canada indeed brings it back in Jan 2027. However, at the moment our best option would be to start a business...which is a slight hassle but not too off-putting lol. Also, not sure my parents would join.
4) Miami - 5%. Return to our previous home in Miami that's currently rented out. We really don't get excited for this at all, but it would be a very comfortable transition. We already know our home, our town, feel really good about our school options there, and have a good number of friends/family. My parents would probably be fine joining us there too. But man, I'd rather not. It just feels meh (I get that we're privileged)
5) Other - 4%. I dunno...loads of other cities we like but I'm not gonna give them serious thought yet. But I acknowledge there's a chance things shift in the coming years.
Long term we really love Taiwan and would expect to come back after the kids become independent. I plan to get my permanent residence later this year which would allow us to live here anytime in the future (provided "Taiwan" still exists). If things continue on their current trajectory, I think we'll be able to FIRE to most places in the world, but it still feels good to know Taipei is one of our favorite places and it's roughly half the cost of our previous life in Miami.