US citizen remote worker, residence card (zairyu card)-holder fiancée. What’s the best way to move AND keep my job?

My fiancée is a zairyu card holder and has been studying/working in Japan since before covid. I currently have a US-based remote job (taxed in US, paid for in USD, to my US based bank account) that does not restrict me to the continental US.

I'm technically eligible for the digital nomad visa, but that involves doing 6-month-on, 6-month-plus-off long distance, which is not ideal.

The two other visas that I know of are:

  1. Student visa: enroll in one of the approved Japanese language school, and try to get through N1 within a year or two. My workload is managable enough that I can juggle both classes and my work. Problems are:

    • I'm pushing mid 30s already. My understanding is that eyebrows would be raised when they receive my visa application.
    • Student visa only allows me to work up to 28 hours a week
  2. Dependent visa: my understanding is that if we are married, I would be eligible for a dependent visa through my wife (her job and income are eligible); however:

    • There's still the same 28 hours/week work limit

My questions are :

  1. Does the 28hr/wk apply to foreign jobs as well? Or is it only for Japan based jobs.
  2. How would JPN Government know if I'm working over the limit (assume US-based job)? Is there a special reporting requirement?
  3. What is the best way forward for us?

by Wutwutwubsy

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