For me, this is not a cut-and-dry, black-white issue.
The Bible has plenty to say about caring for the poor, but IMO, the poor of the Bible are not at all like the poor in 21st century America where there are so many ministries and government agencies to provide for them. Those kinds of ministries/agencies did not exist in biblical times and the poor/homeless were destined to suffer eventual starvation and death from exposure. While this may sometimes occur in modern times, it is far less likely that it will.
Add to that the fact that many people are poor by their own choice or from too many bad decisions or simply an inability to hold a job. These people do not need more financial aid--since their inability to handle finances is the cause of their poverty. Then there are those who live their lives off the charity of others, who go from person to person, town to town, church to church asking for a handout but who will not look for work--these are the ubiquitous church-bums every pastor and charitable organization has to deal with, people who abuse charity and deplete resources needed to help the truly needy.
Then, on the other hand, there are some homeless people who are mentally or emotionally challenged or others, such as children or those who have suffered loss of a job, etc., through no fault of their own. These people deserve all the help they can get.
Bottom line, I will help the poor (but never with money), feed them, buy them clothes, pay their utility bill, buy gas for their car, support the Salvation Army and Love INC, and do what I can for those who are in need, but I will be as wise as a serpent while I am being as harmless as a dove.
~Jim