We live in Vancouver, Canada, which for various reasons (weather, policy effects, etc.) has a large homeless population. Many of them suffer mental illness of some degree. Panhandlers are a common sight on the street. More than once we have been approached by a panhandler inside local restaurants.
Four-year-olds, being four-years-olds, take all this in and notice that there's something going on here out of their ordinary experience. In the same vein, I know they can be very sensitive to adults' discomfort about certain subjects and that can have unpredictable effects—maybe bringing more questions or teaching them there's something wrong or to fear.
My 4yo is clearly struggling with these ideas. He retells one particular incident a few months ago of a panhandler approaching he and his mother while they ate, retelling the events and the conversation he had with his mother just after. He's unsettled, but not fearfully. His mother's approach is to talk with him about the (4yo-level) facts of it—that they don't have anywhere to live, that they're hungry, that they are asking for food or money. That he's still retelling that conversation tells me that he's not figured out what to do with it yet. And understandably so—it's a complicated enough subject for adults, let alone young children.
As the primary caregiver, I get these retellings most often. I don't know how to talk with him usefully about it. I don't want to discourage him and thereby teach him that these are "bad" questions or subjects to think about, but I don't know how to engage with his conversations about it except to affirm his statements. I don't want to be silent either, or not-so-subtly shift him off the subject, because that amounts to the same thing.
How do I talk to a 4-year-old about homelessness and all the related subjects his questions will inevitably include?