The aim of the workshop is to bring together astronomers with the diverse but highly complementary expertise necessary to address long-standing issues in studies of massive galaxies at high redshift. These experts include: observers specializing in multiwavelength observations and large astronomical surveys, theorists who work on hydrodynamical cosmological simulations and semi-analytic models of galaxies at various physical scales, and creators of the most widely-used methods and software for modeling and interpreting these observations. The goal is to produce a whitepaper which raises key questions on these topics for the coming years. We have prepared an engaging program lineup covering nine key areas to address fundamental problems in massive galaxy evolution and inform future directions for the field.