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Historic neighbourhoods in European cities have been gentrified or separated from the everyday life of the contemporary city (e.g., they became either open air museums and tourist destination for sightseeing, short-term letting, or international real estate capital investment ’ghost’ towns), as a result of their strategic preservation from the authorities early on in the 80s and 90s.  However we see that in many south European and Mediterranean historic cities, the urban fabric is a mixture of new and old structures, wherein we identify many examples of culturally-valuable structures which have not been yet listed as protected heritage, as in many cases the authorities lack the policy instruments, or the necessary funds, to proceed with the conservation of these buildings. The space of the historic city has been mostly studied, analysed, communicated and imagined by means of methodologies and tools sourced from the humanities, and traditional architectural drawing tools.  Also, we notice that in many northern European cities, the historic core of the city is fully conserved, preserved, protected and documented already from before the so called digital revolution. These two conditions have arguably limited our capacity to leverage the power of digital tools, data analytics and complexity theory to monitor and understand the development of the cities in real-time.Heritage buildings falling down due to human neglect, inability of local authorities to monitor their condition and environmental pressures, e.g., heavy rainfall in 2019 (Nicosia, Cyprus).Sicily, Italy, 2019.Abandoned patios in the historic centre of Cordoba, Spain, 2018.