I think it might be good to find some people in your area who are already working with the homeless. Also its more important to have quality not quanity interactions. Don't worry so much about numbers. If your willing to listen many homeless people will talk to you at length. 1 to 2 hours. Find out what they might need by talking to them. They may need a pair of socks, but they also need a friend. They'll care more about how you treat them vs what you give them. I helped with a ministry for a number of years in Minneapolis called the Jesus Kitchen. We set up in the same spot every saturday night and fed people and talked to them. We'd have blankets and warm clothes on hand, as well as hot food and coffee. At this point that ministy has been happening for about 15 years. If you want to do something really cool, you could fix up a bike and be willing to literally give a homeless person your bike. If you give someone a bike give them a lock too so they can keep it for a while. Long story longer, if you've never really interacted with the homeless it may be wise to tag along with someone who has.