I don’t give money or material assistance of any kind to the homeless. I don’t believe in it. There are social service organizations better equipped for this. I talk to the homeless at times. I know some of their names. There are a few I take time to greet and we’ll have brief chats. But I prefer to keep the unwashed at a distance — be they homeless or not.
The homeless are one reason I am not a libertarian (even though I have a lot of sympathy for that way of thinking, it comes from my UCLA economics education and my admiration for almost all things Milton Friedman). They are one reason I am not opposed to the prohibition of alcohol, drugs, prostitution, pornography etc (I don’t support such prohibitions either).
If we make vice (and in my view most homeless have destroyed their own lives with drugs and alcohol and bad decisions) easily available, a lot of people will indulge and a significant portion of them will destroy their lives and become a burden on the rest of us.
I no longer believe that what consenting adults do in the privacy of their own homes is their business alone.
Everything we do affects other people. If we choose to spend our spare time watching pornography or doing drugs or studying Shakespeare, that is going to affect us and those around us.
In one of the evening prayers, we thank G-d for separating us from those who stray.
Judaism is an exclusivist religion, and the more seriously it is practiced, the more exclusivist it gets. The Modern Orthodox are more exclusive (many won’t invite non-Jews to their seders for instance because it is problematic as far as Jewish law, a non-Jew pouring wine for a Jew etc) than the non-Orthodox and the traditional Orthodox are more exclusive than the Modern Orthodox.
It tends to be the modern Jews who get all weepy about connecting with non-Jewish blacks while the traditional Jew is little concerned with this and more concerned with fulfilling his obligations as a Torah-observant Jew (and none of these obligations entail davening in black churches).