Using evidence from the physical remains of the city as well as from excavation archives, scholarly publications, and ancient legal texts, my dissertation is the first project to index, quantify, and analyze urban property investment at Pompeii on a citywide scale. It simultaneously investigates the related phenomenon of complexity, a term here used to characterize the increasing regularization and interrelatedness in the built environment of Pompeii. The central question under investigation is: was urban property investment at Pompeii a sidelined, opportunistic endeavor bound up with subordinate social relationships, or was it a primary, strategic economic concern, and if so, to whom?