A commonly held belief among educators, researchers, and students is that high-quality texts are easier to read than low-quality texts, as they contain more engaging narrative and story-like elements. Interestingly, these assumptions have typically failed to be supported by the writing literature. Research suggests that higher quality writing is typically associated with decreased levels of text narrativity and readability. Although narrative elements may sometimes be associated with high-quality writing, the majority of research suggests that higher quality writing is associated with decreased levels of text narrativity, and measures of readability in general. One potential explanation for this conflicting evidence lies in the situational influence of text elements on writing quality. In other words, it is possible that the frequency of specific linguistic or rhetorical text elements alone is not consistently indicative of essay quality. Rather, these effects may be largely driven by individual differences in students' ability to leverage the benefits of these elements in appropriate contexts. This dissertation presents the hypothesis that writing proficiency is associated with an individual's flexible use of text properties, rather than simply the consistent use of a particular set of properties. Across three experiments, this dissertation relies on a combination of natural language processing and dynamic methodologies to examine the role of linguistic flexibility in the text production process. Overall, the studies included in this dissertation provide important insights into the role of flexibility in writing skill and develop a strong foundation on which to conduct future research and educational interventions.