The toughest thing is that people working in Japan from the US have to secure employment before leaving the US. I wish we had working holiday visas, but, so far, the US and Japan haven't come to agreement on such things. I may talk to the folks in the Los Angeles offices of The Japan Foundation later...to see if they have any sage advice on the matter. The main social problem seems to be that the school operators think that a position teaching English is "below me," and that staff is somewhat uncomfortable with having a "junior" who is so "senior."
This is one area that respect for elders actually works against you.
I do have experience working for a Japanese company before though. I worked for Mitsubishi Electronics America back in the 80s...so I do know how to "behave."