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.

The wages are also very low for computer programming compared to the US, despite a cost of living that is not much lower.