This paper presents some steps in experimentation aimed at describing urban spaces made following the series of earthquakes that affected a vast area of central Italy starting on 24 August 2016. More specifically, these spaces pertain to historical centres of limited size and case studies that can be called “problematic” (due to complex morphological and settlement conditions, because they are difficult to access, or because they have been affected by calamitous events, etc.). The main objectives were to verify the use of sets of heterogeneous data that are already largely available to define a workflow and develop procedures that would allow some of the steps to be automated as much as possible. The most general goal was to use the experimentation to define a methodology to approach the problem aimed at developing descriptive responsive models of the urban space, that is, morphological and computer-based models capable of being modified in relation to the constantly updated flow of input data.