Elastic optical networks (EONs) operating in the C-band have been widely deployed worldwide. However, two major technologies—multiband elastic optical networks (MB-EONs) and space division multiplexed elastic optical networks (SDM-EONs)—can significantly increase network capacity beyond traditional EONs. A one-time greenfield deployment of these flexible-grid technologies may not be practical, as existing investments in flexible-grid EONs need to be preserved and ongoing services must face minimal disruption. Therefore, we envision the coexistence of flexible-grid, multiband, and multicore technologies during the brownfield migration. Each technology represents a tradeoff between higher capacity and greater deployment overhead, directly impacting network performance. Moreover, as traffic demands continue rising, capacity exhaustion becomes inevitable. Considering the different characteristics of these technologies, we propose a robust network planning solution called Progressive Optics Deployment and Integration for Growing Yields (PRODIGY+) to gradually migrate current C-band EONs. PRODIGY+ employs proactive measures inspired by the Swiss Cheese Model, making the network robust to traffic peaks while meeting service level agreements. The upgrade strategy enables a gradual transition to minimize migration costs while continuously supporting increasing traffic demands. We provide a detailed comparison of our proposed PRODIGY+ strategy against baseline strategies, demonstrating its superior performance.