Over the past couple months, Henry really started to notice and talk about all the homeless people we pass on the street. Although we try to keep his world mostly positive during the first plane of development (during which he is developing his love for the world), we also want to be honest with him about what he sees.
It was very clear to us that he was feeling sympathy for the homeless people we pass by each day, so we wanted to enable him to do something to help the situation. We decided that what made the most sense for our family (given that we live in Central Texas where the sun and heat are relentless for most of the year) was to pass out water bottles.
We keep a shoebox filled with bottled water next to Henry's carseat and Henry passes it out his window when we stop at a stoplight next to a homeless person. We've been doing it for a couple months and it's been working out really well for our family.