Challenges
The idea of a little "challenge" inside each box comes from a friend who was homeless in both Australia and US at two points in his life, and said the most useful volunteer organization he attended was the poorest funded. They didn't give food, nor ask people to tell stories of woe... they just met once a week to give some challenges for the next week - little achievable tasks like getting a new pair of shoes etc.
I have written the challenges below off the top of my head, ultimately I want to hear from people without homes, or experts in charity about what challenges might be most useful and best received.