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This paper presents a large anonymized dataset of homelessness alongside insights into the data-driven rehabilitation of homeless people. The dataset was gathered by a large non-profit organization working on rehabilitating the homeless for twenty years. This is the first dataset that we know of that contains rich information on thousands of homeless individuals seeking rehabilitation. We show how data analysis can help to make the rehabilitation of homeless people more effective and successful. Thus, we hope this paper alerts the data science community to the problem of homelessness.