This study presents cascaded thermodynamic and environmental analyses of a high-performance academic building. Five different energy efficiency measures and operation scenarios are evaluated based on the actual measurements starting from the initial design concept. The study is to emphasize that by performing dynamical energy, exergy, exergoeconomic, and environmental analyses with increasing complexity, a better picture of building performance indicators can be obtained for both the building owners and users, helping them to decide on different investment strategies. As the first improvement, the original design is modified by the addition of a ground-air heat exchanger for pre-conditioning the incoming air to heat the ground floors. The installation of roof-top PV panels to use solar energy is considered as the third case, and the use of a trigeneration system as an energy source instead of traditional boiler systems is considered as the fourth case. The last case is the integration of all these three alternative energy modalities for the building. It is determined that the use of a trigeneration system provides a better outcome than the other scenarios for decreased energy demand, for cost reduction, and for the improved exergy efficiency and sustainability index values relative to the original baseline design scenario. Yet, an integrated approach combining all these energy generation modalities provide the best return of investment.