[Sangetsu]

Your situation is difficult because everyone wants a job in Tokyo. Having a girlfriend makes it even more difficult, as the odds of you and her being hired from overseas and getting a job in the same prefecture (let alone the same city) are extreme, to say the least.

When I first applied for a teaching job in Japan I was told not to bother requesting Tokyo, as positions in the city were filled by teachers with more seniority. However, the company I applied to was impressed during my interview, and I was offered a position at their top school in Ginza. That might sound good, Ginza is a great place, but it's expensive, and the nearest housing in my school's price range was a 45 minute commute away, and even then, it was expensive.

Your best bet would be to explore you second option, which is to go to Japan on your own, rent a place temporarily (you won't be able to get a real apartment without a job and an alien registration card), and go out and apply at as many places as you can. You'll need to bring a lot of money, at least enough to get you through 4 or 5 months. It will take time to find a job, time to get a visa, and time for your first paycheck to be processed (up to 8 weeks, if you are unlucky).

You'll need to find a job as soon as possible so you can get your work visa processed within the 90 days you have on your tourist visa. It used to be possible to leave the country before the 90th day, then return and get another 90 day visa, but immigration has clamped down on this practice.

It's pretty much a certainty that you and your gf will not work in the same school (and probably not for the same company), but you ought to be able to find jobs close enough to commute to from the same place.

As for myself, I live in Chiba now, and I'm happy here. I spend my weekends in Tokyo, but enjoy the quiet life here in the country next to the beach. It's laid back, inexpensive, friendly, and the surfing is great in the summer.