There is a growing recognition that physical and social disorder and other neighborhood conditions play an important role in shaping the attitudes, behaviors, and well‐being of residents. Most research that seeks to measure neighborhood conditions relies on census or survey data, yet systematic observation often provides a more objective measure of observable neighborhood conditions. However, almost all of the research that has used systematic observation to measure neighborhood conditions has been conducted in developed nations. We describe the conceptual and methodological issues that arose during our use of systematic observation to measure disorder and other neighborhood conditions in Trinidad and Tobago, a two‐island Caribbean nation. Adapting this methodology for use in a distressed community in a developing nation raised challenges not yet addressed in the literature. We describe these issues and reflect on the applicability of systematic observation techniques and current conceptualizations of disorder across different contexts.