The article focuses on other aspects that are important, but is not hacking.
It seems to me that homelessness IS a hack on the regular system. And the way he writes about what happens is informed by his intelligence and his programmer background. To me, the idea of a homeless guy running sims to develop his solution to efficient routing of a traveling salesman while not having a place to plug in his laptop which is his own is pretty hacky.
Maybe this article isn't EVERYTHING you would want in a clever and enjoyable read from a homeless programmer, but it may be the best out there in this genre. This was not a New York Times reporter playing a homeless person, this is the real thing. BTW, I worked with this guy briefly, so I know he is the real thing.