The purpose of this article is to understand the function, logic, and impact of qualitative systems for analyzing text complexity, focusing on their benefits and imperfections. We identified two primary functions for their use: (a) to match texts to reader ability so that readers read books that are within their grasp, and (b) to unearth, and then scaffold, those features of specific texts that are likely to present challenges for readers of differing abilities. We examine three approaches to qualitative text analysis (text-leveling systems, rubric and exemplar systems, and text-mapping systems) relative to these functions. We conclude by strongly advocating the use of qualitative systems, if only to prevent the unchecked use of quantitative approaches from promoting invalid applications of text complexity. In the same breath, we raise a set of vexing issues that the field must address if these approaches are to be used with confidence.