It seems to me that being an expat in Japan is a win win with no downside, as one can enjoy everything that works within their society while avoiding all the social pressures the Japanese suffer.
We are planning a trip soon to investigate our insight.
Haven't been there, but anecdata from my friend who spent 2 years there says yes, but you have to probably work remotely, because Japanese companies are very rigid, hierarchical and conservative - culture clash might be hard and you might be suffocating.
Agreed. But working remotely from Japan can be a great lifestyle if you can pull it off. Almost all of Japan's downsides come from working for traditional Japanese companies.