Tokyo is pretty expensive, and transportation is also really expensive. I'm paying about $550 for rent at the moment (11m^2, shared restroom/shower) "inside" of Tokyo. I got really lucky finding my place though, most equivalent places around here go for at least $100 more a month. If I were working in Shinjuku, it would probably cost me $100 a month for a commuter pass. Internet is pretty cheap though (you can get a home line for about $30 a month).
Still seems to be a bit of a losing proposition, though.