Got offer at a remote Japanese company — should I move to Japan?

First of all, thanks everyone on this subreddit for all your wisdom. I am currently navigating a big change and the advice on here has been really helpful with initial conversations. Would really appreciate some constructive feedback.

Background: I am currently living in US and considering moving to Tokyo since my partner has moved there for work. I recently quit my corporate job in US to go full freelance. I have two big clients — one based in the US and one based in JP. Both offered me remote, full-time positions (and JP work visa for the latter) after hearing I quit my corporate job.

Compensation details: I am still actively negotiating with both companies and struggling given the insane flexibility. My general situation is as follows:

  1. Current freelance compensation is $100k (3:1 ratio of US vs JP company) with $25k expenses
  2. FT compensation is roughly triple the freelance comp for both companies
  3. Much earlier this year I incorporated a startup (for separate reasons from the freelance work)
  4. Both full-time contracts come with basic insurance coverage
  5. The JP startup will also provide marginal lifestyle perks such as language, commute benefits, and a JP tax advisor
  6. Neither offer includes equity or 401k
  7. I have no substantial investments/assets in the US
  8. Both are ok with me freelancing while working FT

The plan:

  • Finding a CPA ideally familiar with JP tax laws (not financial planner after seeing all the warnings on this subreddit)
  • Using my current S-corp for freelance work (or establish a separate LLC if not possible to reuse)
  • Leaning towards taking the FT offer from US company and freelancing for JP company
  • Live in JP under work visa (but flexible if it's a huge tax disadvantage)

by ingowpo

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