Theory and application of damage stability followed over the years two dissociated paths: static assessments and dynamic simulations. The first approach, being easy to apply and understand, has been preferred by ship designers and regulators; the second, more advanced and first-principle oriented, has been mainly reserved for research or high-level consultancy, especially for passenger ships. Nowadays, the availability of numerical flooding simulation tools across the scientific community and calculation power in the industry allows for a possible definitive transition of damage stability assessment towards direct numerical analyses. However, research should softly drive designers towards more advanced processes via a suitable didascalic calculation framework. The multi-level approach pursued in project FLARE is an example of such a transition from static to dynamic damage stability assessment. The present work initially carefully reviews the probabilistic concept of damage stability, critically comparing the prescriptive statistical methods with direct ones and providing insights and guidance on how researchers and designers can reconcile with the original implicit assumption of the probabilistic approach. Secondly, the development of the multi-level framework highlights incongruences concerning modelling of damages between static and dynamic assessments, disfavouring the comprehension of dynamic results to designers. Two detailed examples highlight the differences in dynamic simulation results between different damage breach modelling, leading to completely different flooding paths for the same damage case. Finally, the paper indicates how a compromise between academic approach and application could help designers to start their transition towards direct numerical damage stability analyses.