The word "homeless" may conjure up images of single adults living on the streets. Yet, families with children also experience homelessness, and their residential instability often impacts how and where their children experience school. In 2011, I was part of a research team exploring how family homelessness and its diverse residential contexts shaped schooling experiences in a medium-sized urban community. We analyzed school and community artifacts, examined district-level data, and conducted semi-structured interviews with parents, community providers, and school actors. As part of this larger study, I also explored school-family and community partnerships in the contexts of homelessness and high mobility. In this SAGE Research Methods case, I examine some of the challenges we confronted while working on this multi-year, qualitative case study. In particular, I highlight the complexity involved in gaining access to participants and building rapport with wide-ranging actors. I foreground a number of strategies we used to help overcome these challenges and provide practical lessons for researchers interested in case study design. [This content is provided in the format of an e-book.]