Broadly, this dissertation seeks to contribute to studies of post-war reconstruction, with an emphasis on Ukraine as it is situated within the Black Sea region. An initial survey of the literature on post-war reconstruction for Ukraine identified issues around how to better understand, via modeling, the process of reconstruction as enacted by actors who share different visions (i.e., spatial imaginaries) of the future built environment. These issues can be summarized as the following: (i) understanding why regions cohere, mobilize, or fragment, (ii) studying how regions change in response to shocks, and (iii) articulating which actors collaborate, and how, to form – or reform – regions. Literature gaps identified for each issue include producing a framework for collective mental representations (e.g., spatial imaginaries), characterizing infrastructure network transformations in response to shocks, and simulating reconstruction actor collaboration under diverse constraints. Chapters two through four provide self-contained research papers for each of the three aforementioned literature gaps. The first chapter highlights the methods of the papers, briefly discusses the results, while chapter five discusses a future project that integrates, and builds on, the three papers to produce a realistic simulation of post-war reconstruction in Ukraine.