Since you said you're going to Osaka, Kyoto and Tokyo, then I highly recommend the Japan Rail Pass. (The bullet train or Shinkansen is so much fun to ride.) You also need to purchase your rail pass
BEFORE you arrive in Japan. You'll save hundreds, literally. The JRL is good for just travelling between suburbs in Tokyo too. All you have to do is flash your pass and passport going through the handicap turnstile and board whatever train you want. No standing in long lines trying to figure out how much it is from one station to the next.
Also, I highly recommend a day trip to Kamakura. Just board the train (I think it's track 14.) to Kita-Kamakura but get off at Kamakura. This will take you to the big Budha and lots of area temples.
Don't worry about the language barrier. Most of the people I encountered spoke some English. And when in doubt shopping, everyone seems to speak the international language of VISA. Although, if you use your VISA at a Mandarake, they'll ask if you want 1 payment or 2.
ALWAYS say 1! If you don't, you'll have to come back another day to get your merchandise.

There's also a lot of signs in the Tokyo area that are in English so that'll help.

You'll get very use to seeing the same kanji over and over again and be able to figure it out. I learned to read open and close while I was there.
Most importantly, have a blast and post pictures!
--Forgot one thing, do your homework on hotels too. We stayed in the Prince at Shinigawa for about $100 a night. And then that was split in half since there were 2 in a room. So in other words, you can find some really good rates.
