This paper presents an assessment approach to fostering socioeconomic re-development and resilience in Iraqi regions emerging from the destruction and instability, in the aftermath of the war conflict in Iraq. Focusing on the intricate interplay of logistics infrastructure and economic recovery, the present study proposes a novel framework that integrates general resilience insights, data analytics, infrastructure systems, and decision support from Data Envelopment Analysis (DEA). We draw inspiration also from historical cases on “creative destruction” or “Blessing in Disguise” (BiD) phenomena, like the post-WWII reconstruction of Rotterdam, so as to develop the notion of stepwise or cascadic prosilience, analyzing how innovative logistics systems may in various stages contribute to economic rejuvenation. Our approach recognizes the multifaceted nature of regional resilience capacity, encompassing both static (conserving resources, rerouting, etc.) and dynamic (accelerating recovery through innovative strategies) dimensions. The logistics aspect spans both the supply side (new infrastructure, ICT facilities) and the demand side (changing transportation flows and product demands), culminating in an integrated perspective for sustainable growth of Iraqi regions. In our study, we explore several forward-looking strategic future options (scenarios) for recovery and reconstruction policy factors in the context of regional development in Iraq, regarding them as crucial strategic elements for effective post-conflict rebuilding and regeneration. Given that such assets and infrastructures typically extend beyond a single city or area, their geographic scope is broader, calling for a multi-region approach. By leveraging the extended DEA approach by an incorporation of a super-efficiency (SE) DEA approach so as to better discriminate among efficient Decision-Making Units (DMUs)—in this case, regions in Iraq—our research aims to present actionable and effective insights for infrastructure investment strategies at regional-governorate scale in Iraq, that optimize efficiency, sustainability and resilience. This approach may ultimately foster prosperous and stable post-conflict regional economies that display—by means of a cascadic change—a new balanced prosilient future.