Tokyo life is more expensive than many parts of the US, maybe not the bigger cities though. Entertainment here is crazy expensive (drinking and eating out, performances and events, sports and music etc.), while things like rent are slightly cheaper. Food at the market is similar but the 100 yen shops make most simple household items (from soap to cups to stationary) much cheaper than the US.

In America, health insurance and education just keep going up to the point where it's getting difficult to think about the future. I'm sure if you work online and live in a low population area it's easier, but visas are always annoying.

$250 a day is a lot anywhere I think....there may be a handful of countries where it's not, Scandanavia? Maybe? But even there I'm sure it's enough to live and eat and afford stuff you need.

The world is a big small place, I'm sure there are many places you'd like for different reasons. Japan isn't the easiest place to live, tiny houses... sometimes I think about moving to Thailand, Indonesia, Nepal, Portugal or Spain.....but I really feel like myself in some parts of Tokyo and I feel my personally fits here, I'm an alien to them, but not a typical foreigner and not difficult for the local people to relate to. We will see in 2-4 years when we are thinking about possible making little people.