A personal account of a program of research on homelessness and poverty spanning the past 20 years is provided, with a focus on the many methodological, practical, and ethical difficulties encountered. Interesting discoveries and enjoyable aspects of the research process are also presented. Several role conflicts that arose for the researcher in this community-based work are also described, and the importance of nurturing long-term personal relationships with various community leaders is emphasized. The evolution of research ideas is documented by highlighting how the findings and problems encountered in earlier studies led to improved methods and new research questions.