I`ll try to help you out here.
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*Basic Academic Standards of Japanese schools
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What type of schools? Elementary schools? Middle schools? High schools? Universities? Japanese language schools? I can`t really help until I know which. ^^;
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*The "best" and most affordable city to live in (for someone who plans on having things to do most all the time) with pretty good transportation
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I would personally say Nagoya - which is why we live here. It`s the third largest metropolitan area in Japan, but yet isn`t nearly as crowded and hectic as Tokyo or Osaka... But you still get all the great amenities of living in a big city, right in the middle of Japan. To the east is Tokyo, to the west is Osaka. We have a great public transportation system, plus it`s much much much cheaper to live here.
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*Which would be smarter/more affordable...visiting Japan for a month to 5 weeks or just living there?
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This more depends on your visa than anything else. If you have the means to get a proper visa, I would say living here would be more "smart". You would be able to rent a proper room, etc, and it would end up being less than a hotel.
If you really only can manage to stay a month or so, hotel and food costs (as you`ll have no kitchen in a hotel - all eating out) will REALLY add up. I would guess that 9 months to a year of living in an apartment would be relatively equal to 5 weeks in a hotel.
Trying to rent an apartment for 4 or 5 weeks would probably be impossible, and even if they let you, you`d still have to cover all the costs of starting new utility accounts, etc plus regular deposits for everything. It isn`t much if you were to spread it out over 9 months or a year, but for one month it would be a complete and total waste.