The ability to reliably create a low-entropy gas of polar molecules is essential to creating a quantum simulator of ultracold polar molecules. These systems feature long-range and anisotropic dipolar interactions, and as quantum simulators host exotic quantum phases as well as as a diverse range of phenomena ranging from quantum magnetism , to many-body localization, to synthetic spin-orbit coupling. However, despite intense experimental efforts, a robust experimental pathway to low-entropy states has remained out of reach. In this talk we use Path Integral Quantum Monte Carlo (QMC) simulations, as well as analytic techniques, to consider how the combined effects of interactions, temperature, and adiabatic loading hinder the ability of creating a low-entropy gas of polar molecules in an optical lattice. Additionally, we propose how quasi two-dimensional layered configurations of dipolar lattice gases can be used to stabilize novel quantum phases. Finally , we use a novel extension to the Path Integral QMC simulations to include the effects of dissipative coupling to a reservoir on the system. While dissipation is naturally present in ultracold molecule experiments, we show that an engineered dissipation allows one to realize a many-body analog to the spin-boson model as a tool for the observation of dissipation-induced phase transitions.