When it comes to giving, one excuse I hear quite often is, How do I know that homeless person isn't faking it? How do I know they aren't going to spend my $1.00 on alcohol....bla bla bla. Jesus dodn't tell us to do a background check before we give, he simply said that When we do to the least of these, we are doing it as unto him.
But anyway, if it makes you feel better, you can try this outreach. Have bags prepare and stored in your car to give away to the homeless. Some items that can be out in your homeless kits include: Toothbrush/Toothpaste, socks, Tylenol, gospel of John, Water, band aids and whatever else you think would be useful. These are a great way to spread the gospel in love!