This article focuses on the methodological lessons learned while conducting a legal research study of the lower criminal courts by gathering observational and interview data to understand why many defendants charged with misdemeanor or summary offenses proceed without counsel. The present study describes the socio-legal methodology employed and draws from project memorandums and research assistants’ field notes gathered during court observations and written reflections following defendant interviews. The present article addresses the methodological obstacles and lessons learned from gathering complex data on rights waivers and focuses on how we might improve the legal study of the lower criminal courts and answer critical constitutional and procedural questions by improving our legal methods.