Just watched the documentary Japan: A Story of Love and Hate.
I read a lot of stories like these every once in a while. Once thing that strikes me is how alone they are – no family, little friends. Back home, I’ve met (and known) some people who are a lot poorer and worse off than Naoki in the story, but I somehow feel they are more content. Happier even.
Here’s the documentary playlist on youtube and the post on Tokyo Times.
Homeless Person in Shinjuku. (click on the photo for a larger view)

Commenting here is easier than twitter, so I thought I’d pass along some links on the situations of the homeless in Japan.
I used to live in Kitakyushu and was always amazed at the way most of the homeless there formed groups to share food and drinks. Kitakyushu is also a bit of an oddity in Japan, though, as it has a lot more support for the homeless by NGOs — in large part due to mistreatment from the city government. see http://search.japantimes.co.jp/cgi-bin/nn20071212a7.html for some details on that. From what I understand the government is trying to improve things but every few months now it seems there’s another scandal from the city not paying benefits and such.
In Tokyo, it’s fairly common to see homeless groups in Ikebukuro, and I expect it’s largely true elsewhere in the city. See http://search.japantimes.co.jp/cgi-bin/nn19970501a4.html for an example of Shinjuku govt. action and homeless groups responding
This BBC series http://news.bbc.co.uk/2/shared/spl/hi/asia_pac/04/japans_homeless/html/1.stm shows one particular case of community forming in Osaka.
Also see http://www.csmonitor.com/2004/1018/p07s01-woap.html which is less a case of government failing and more of a societal issue.
Although it is only anecdotal, I used to talk with students (I used to teach English here) about homelessness (you see a few thousand students and the subject comes up occasionally). I was always amazed at the distribution of opinions. There were some who recognized the ways in which society had failed them, but the majority of students saw it as being the result of laziness or even choice.
I haven’t, yet, seen the documentary you refer to. I’m curious to see what, if any, conclusions they come to.