If you live on the streets, and smell, you will find it difficult to enter 'polite' society.
I think some of our caution here is because there are many services already established for giving to the poor. Some people choose not to use them, but they are there.
In the US, beyond severance pay for unemployment we have unemployment insurance, and jobhunting centers with many services.
http://statisticbrain.com/welfare-statistics/
We have social security for retirement or the loss of a household breadwinner;
the welfare system and food stamps. A large percentage of citizens are using public assistance.
There are welfare-to-work programs, Americorp, Jobcorps; VESID and other programs for retraining those with disabilities; state programs providing almost-free health insurance; tuition assistance.
http://greenbook.waysandmeans.house.gov/2012-green-book
Then there are private organizations: Catholic Family Services, Salvation Army, Volunteers of America, Goodwill, Operation Blessing, Lion's Club, Samaritan's Purse, Jerry's Kids, McDonald houses, many local food distribution services, and the generous work of each private church -- and non-Christian religious organizations.
Our society is loaded with generous and supportive activity.
I have seen overseas magazines that pumped up Obama's statements on how broken our system is, but in reality it's incredibly functional and generous to people in need.
A homeless person can stay at each homeless shelter for a limited amount of time. They can revolve from one to the other -- in the cities, they are within walking distance of each other. Each large city also provides subsidized housing, so it's a matter of applying for it -- and some people choose not to.
One option I heard of was taking a pencil box, or a pencil bag and putting travel size shampoo, tooth brushes, hair brushes, toothpaste, a sewing kit, pen, paper pad, washcloth, soap, and maybe a treat like candy or something, maybe a 5 dollar gift card to Subway or something, putting it in your glove box, or purse/briefcase and handing them out.
Good idea. I've given food to people before, and they say, "What would I want with that?" (Alcoholics don't each much.)
One time it was a person I later saw on the town's
Wanted postings -- showing that some people don't want to be found.
But back to giving as a Christian, yes -- Jesus was clear on it, and the Laws of Moses were too. We are not to love our own lives so much that we would deny others a blessing. Life is not a competition, in the kingdom of God. When we leave this earth, all those possessions mean nothing.