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@twhi Remitting in my case means transferring proceeds from a stock sale to a financial instrument - bank, credit card, etc - that I can use to purchase goods and services in Japan. Are you suggesting that remitting any amount of money - in my case, from stock sales completely unrelated to a...

@twhi To clarify my original point: I'm pretty sure that by design, there's no way to remit money from a Roth Conversion in the same tax year that the conversion was performed, making this tax-free from the U.S. as well as the Japan perspective for NPRs. Or at least, remitting money wouldn't...

Regarding Roth Conversions (question 4), this was asked on Ben's podcast 8 months ago: https://www.youtube.com/live/iuZiI9E2Nvg?si=Fhkfu114FEgMpIBL&t=3531 It seems that if you're NPR, you wouldn't be taxed on the conversion, unless you remit the money to Japan. But remitting would defeat the...

@twhi I'd planned on working on an HSP here initially, but I've just realized that I like the freedom that comes with not working. Maybe my perspective will change within two years. Indeed, the jump from zero to 20% is likely what's bothering me. If I already had to pay capital gains tax in...

@kristhuy In the end I decided to move 2 years worth of living expense (plus some buffer) to my JPY Wise account before moving to Japan, without any further remittances from the moment I set foot in Japan. I believe this means that I won't have any tax liability in Japan when I do capital gains...

@twhi What I meant was in my credit card, or JPY account, which uses local banks as a proxy. Something like Wise or Revolut.

@twhi OK, so if this is true, then this is a new critical detail that I've found nowhere else in my research. My read of this is that if I transfer any amount of cash from my brokerage to JPY in a given tax year, then all the capital gains in my brokerage become taxable in the same tax year...

@twhi Thanks for your point-by-point answers. Some follow-ups: I was talking strictly about capital gains harvesting. In this scenario, you don't remit any money to Japan, you simply sell stock and buy again to increase your cost basis. Crucially, in this case, none of the stock that I'm...

(NB: I've already reached out to tax professionals, just curious what knowledgeable folks here think in the meantime.) My partner and I are studying on a student visa for 2 years in Tokyo. Our budget is $40,000 the first year, and $40,000 * 1.03 (3% inflation factor) the second year. We have...