Urban energy systems are becoming more complex due to the integration of renewable energy sources and electrification of heat supply. Dynamic planning and operation strategies are necessary to optimally satisfy energy demands, especially in the 5th generation of heating and cooling networks, which efficiently address these challenges through decentralized water-water heat pumps. An end-to-end tool chain is presented which enables to analyze and evaluate such systems in early planning phases with limited data availability. It includes thermal building simulations, heating network simulations, optimization, and incorporation capabilities for model-based operation algorithms and AI-based forecasting algorithms. User acceptance of the energy system can also be considered in the design phase in future. This paper presents the interaction of the open-source tools: TEASER, which generates high-resolution time-series of heating and cooling demands of buildings; uesgraphs, which generates and simulates thermal networks from geodata; and EHDO, which optimizes energy hub designs. Future research pathways include integrating AI-based operation optimization and surveys to support user feedback integration. Work will also address substation models for the 5th generation heating networks and novel data infrastructures. The tool chain has already been successfully used in many scenarios, but open questions remain around integrating the methods into the operation phase and further developing the complex energy models the tool chain is built upon.