This work aims at introducing structural sensitivity analysis capabilities into existing commercial finite element software codes for the purpose of mapping retrofit strategies for a broad group of structures including heritage-type buildings. More specifically, the first stage sensitivity analysis is implemented for the standard deterministic environment, followed by stochastic structural sensitivity analysis defined for the probabilistic environment in a subsequent, second phase. It is believed that this new generation of software that will be released by the industrial partner will address the needs of a rapidly developing specialty within the engineering design profession, namely commercial retrofit and rehabilitation activities. In congested urban areas, these activities are carried out in reference to a certain percentage of the contemporary building stock that can no longer be demolished to give room for new construction because of economical, historical or cultural reasons. Furthermore, such analysis tools are becoming essential in reference to a new generation of national codes that spell out in detail how retrofit strategies ought to be implemented. More specifically, our work focuses on identifying the minimum-cost intervention on a given structure undergoing retrofit. Finally, an additional factor that arises in earthquake-prone regions across the world is the random nature of seismic activity that further complicates the task of determining the dynamic overstress that is being induced in the building stock and the additional demands placed on the supporting structural system.