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!

This is a tactic that I think is so cool!!!

A friend of mine, who is very shy was trying to think of ways to spread the gospel and not draw attention to himself. SO he pulled out a phone book and picked random names and addresses.

He would send out a letter with no return address or with a corny return label like "heaven express" or something.  
In the envelope he would place a tract, and depending on what the Lord lead him to do , sometimes he would put food gift cards, money or just a hand written letter. 

Many people find this hard, because they want to see immediate results or be able to tick a box with how many people they "lead to the Lord". With this method, you never know what impact the planted seed will have, at least until we reach eternity!