[midoridensha]

>For example could I, as a US citizen, work remotely for a US company while living in Japan indefinitely (not necessarily permanently, but at least as an option)?

NO.

You must have a work visa to live here, and you won't get that unless a Japanese company sponsors your visa. A US company can't do that for obvious reasons, unless it's a company with a Japanese branch office.

The only way to do what you ask is to get permanent residence first, but that means living here for a while on a work visa or spouse visa.

Also, on top of this, the US company may have issues with you living outside the US while working for them, but that'll be the case for any other country. This was discussed within the last week or so here on HN.

[suggestion]

I figured that might be the case, thank you for the information. I think I would struggle to adjust to the Japanese work culture in order to establish residence within these constraints.

I also pretty much exclusively have software experience in government contracting so the jump to commercial would be pretty big too.

[midoridensha]

>I think I would struggle to adjust to the Japanese work culture in order to establish residence within these constraints.

Or you can work at an American company like Google (not sure if they're still hiring though; I thought I read they had a company-wide hiring freeze).