In my city, we have tons of homeless shelters and help for anyone that needs it. Yet, many choose not to live in these shelters and live on the streets because they don't want to follow the rules of the shelters...which aren't really that strict.

People don't decide to remain homeless based on a rational cost/benefit analysis. It seems to be more of a case of such people being trapped within their psychological limits. This is what happened to Leo, the homeless man in question. From the article:

"When Business Insider caught up with Leo months after the successful launch of his self-made and self-coded app, Leo was still homeless. It seemed he didn't want access to the money that was available to him, which was being held in McConlogue's account. It was too overwhelming."

I'm sorry, but I'm going to have to down vote you. Since personal opinions that people don't agree with seem to be down voted, I'm going to jump on the bandwagon.