In this talk I will discuss open questions in our quest to understand the stellar systems that punctuate the end of their lives via spectacular supernova explosions. Solving the puzzle to connect stellar systems to their final fate has important ramifications for understanding the chemical enrichment of the Universe and galactic evolution and feedback, and these explosions will be discovered in unprecedented numbers by the upcoming Vera C. Rubin Observatory's Legacy Survey of Space and Time (LSST). I will highlight Type Ia supernovae and discuss recent discoveries and an exquisite set of observations obtained by the Zwicky Transient Facility (ZTF). We have recently identified a new subclass of peculiar Type Ia supernovae that provides strong evidence for the explosion of a (relatively) low mass white dwarf star. As part of this work, we recently connected several different machine learning models to produce the first fully automated observation, identification, request for follow-up, spectroscopic classification, and public announcement of the discovery of a new supernova. To close I will discuss a new project, the La Silla Schmidt Southern Survey (LS4). LS4 will complement observations from LSST by providing observations of bright and fast transients that will be missed by LSST.