Often, research projects are presented as final products with the methodologies cleanly outlined and little attention paid to the decision-making processes that led to the chosen approach. Limited attention paid to these decision-making processes perpetuates a sense of mystery about qualitative approaches, particularly for new researchers who will likely encounter dilemmas and uncertainties in their research. This paper presents a series of questions that assisted one Ph.D. student in making key methodological choices during her research journey. In this study, a collective case study design informed by constructivist grounded theory data analysis methods was used to develop a framework of community development from an occupational therapy perspective. Ten methodological questions are proposed regarding research question development, research paradigm, design and analysis, and trustworthiness. Drawing on examples from this research project, these questions are used to explicate the decisions made "behind the scenes," with the intention of providing both theoretical and practical guidance to others embarking on similar research journeys. (Contains 5 tables.)