The final stages in the evolution of the most massive stars play a crucial role in astrophysics, injecting energy and enriched metals into the interstellar medium, and producing compact objects – neutron stars, black holes, and the wide range of transient phenomena associated with them. The predictive power of theoretical models for massive stars, however, is severely limited by the large uncertainties associated with this regime of stellar evolution. The project will constrain some of the most uncertain processes in massive stellar evolution, such as the efficiency of mass loss and the impact of supernova kicks. This project will develop new tools that can maximize the science extracted from the wealth of data on resolved stellar populations and object catalogs that will be available in the coming decade with the advent of facilities, like the Vera C. Rubin Observatory. The project will also broaden the impact of the research through a mixture of new and well-established outreach projects designed to foster engagement by educators and students in science. The spatially resolved stellar populations in Local Group galaxies will be used to place unprecedented constraints on the evolution of the most massive stars. To this end, the investigators will precisely measure the formation efficiencies and evolutionary timescales (i.e., the delay time distributions, or DTDs), for the main outcomes of massive stellar evolution: Wolf-Rayet and Intermediate Mass Stripped Stars, Blue