As someone who has leaned on friends and family for shelter at various points in life and for various reasons (including mental health), I think the recognition of what this man is doing (going to therapy and trying to get his life together) is really important. Asking for him to chip in in a way that is affordable for him, and still allows for him to save, can definitely go a long way in helping him feel self-sufficient and stay motivated to continue contributing. Great idea about contributing through work, as well! I grouted tiles for lower rent one summer, and the sense of ownership over my home it instilled was awesome.