Advancements to a dual scale Large Eddy Simulation (LES) modeling approach for immiscible turbulent phase interfaces are presented. In the dual scale LES approach, a high resolution auxiliary grid, used to capture a fully resolved interface geometry realization, is linked to an LES grid that solves the filtered Navier-Stokes equations. Exact closure of the sub-filter interface terms is provided by explicitly filtering the fully resolved quantities from the auxiliary grid. Reconstructing a fully resolved velocity field to advance the phase interface requires modeling several sub-filter effects, including shear and accelerational instabilities and phase change. Two sub-filter models were developed to generate these sub-filter hydrodynamic instabilities: an Orr-Sommerfeld model and a Volume-of-Fluid (VoF) vortex sheet method. The Orr-Sommerfeld sub-filter model was found to be incompatible with the dual scale approach, since it is unable to generate interface rollup and a process to separate filtered and sub-filter scales could not be established. A novel VoF vortex sheet method was therefore proposed, since prior vortex methods have demonstrated interface rollup and following the LES methodology, the vortex sheet strength could be decomposed into its filtered and sub-filter components. In the development of the VoF vortex sheet method, it was tested with a variety of classical hydrodynamic instability problems, compared against prior work and linear theory, and verified using Direct Numerical Simulations (DNS). An LES consistent approach to coupling the VoF vortex sheet with the LES filtered equations is presented and compared against DNS. Finally, a sub-filter phase change model is proposed and assessed in the dual scale LES framework with an evaporating interface subjected to decaying homogeneous isotropic turbulence. Results are compared against DNS and the interplay between surface tension forces and evaporation are discussed.