I worked as an ALT for a shitty dispatch company for 2.5 years. I lived in a fairly inaka city (30 min from a metropolis, however), my apartment was a Leopalace (one of the dorm room-sized ones), and I lived 2 hours by express train away from my wife. Now, (two years later) I live in a bustling metropolis in the continental US working in an extremely well-paid entry level job in the field I'd always intended to work in, for a world-famous company. My wife and I left Japan because we felt like we needed to stop playing around and actually start careers before we got too old to be entry-level. By that metric, I should be ecstatic. I have a nice apartment, a large friend group, a great career track, my wife is in grad school, and yet... all I can think of is moving back to Japan.
We're working on a plan that hopefully will end us up back in Japan in a nice situation, but it'll be two years at the minimum. I doubt that I can become proficient enough in my field in two years to beat out a native Japanese speaker (working on N1), and it turns out I have very little interest in working in this field at all. I was happier as an ALT, even with the lack of job security, retirement options, etc...
I suppose the tl;dr is I miss Japan horribly, and I say that having lived in multiple places around the world as a child and an adult. I know the only sensible answer is to wait out the two years and hope our plan pans out, but it's the kind of plan that could also take six years if the right job doesn't pop up... and I'm terrified of sitting around unhappy for two years, let alone six.
Has anyone been in a similar situation? What did you end up doing? There's no good or right answer, so I'm interested in opinions and other people's similar sob stories.