Academic initiatives have become cornerstones in many residential operations on college and university campuses. Despite efforts to enhance academic outcomes of residential students, existing research on residential GPAs reveals either dated or questionable results. Programmatic functions focused on integrating academics into the college living environment--such as living-learning communities, faculty-in-residence, and themed floors--have received a fair amount of attention in recent research, yet course-specific academic support initiatives within residential populations have received little, if any, attention. To fill this gap, this study performed a thought experiment by analyzing course enrollment and grade data for two semesters. Manipulating the actual earned grades in the most frequently registered classes simulated the results of participation in hypothetical course-specific support initiatives during the studied semesters. The results revealed existing value in identifying, and then employing resources to, populations and courses that will yield the greatest impact on GPA. While the assumptions established to manipulate the grades in each of the three most frequently enrolled courses were optimistic (and thus should be considered with caution), the framework of this study demonstrates how the analysis of residential course enrollment and grade data allows for the creation of benchmarks within strategic planning focused on academic success in residence halls. [Discussion questions developed by Denise Davidson and Bryson Purcell.]