Throughout wind energy development, there has been a push to increase wind turbine size due to the substantial economic benefits. However, increasing turbine size presents several challenges, both physically and computationally. Modeling large, highly flexible wind turbines requires highly accurate models to capture the complicated aerodynamic response due to large deflections and nonstraight blade geometries. Additionally, development of floating offshore wind turbines requires modeling techniques that can predict large rotor and tower motion. Free vortex wake (FVW) methods model such complex physics while remaining computationally tractable to perform the many simulations necessary for the turbine design process. Recently, a FVW model—cOnvecting LAgrangian Filaments (OLAF)—was added to the National Renewable Energy Laboratory engineering tool OpenFAST to allow for the aerodynamic modeling of highly flexible turbines along with the aerohydro- servo-elastic response capabilities of OpenFAST. In this work, FVW and low-fidelity blade-element momentum (BEM) structural results are compared to high-fidelity simulation results for a highly-flexibly downwind turbine for varying TI, shear exponent, and yaw misalignment conditions. Through these comparisons, it was found that for all considered quantities of interest, SOWFA, OLAF, and BEM results compare well for steady inflow conditions with no yaw misalignment. For OLAF results, this strong agreement was consistent for all yaw misalignment values. The BEM results, however, deviated significantly more from SOWFA results with increasing absolute yaw misalignment. Differences between OLAF and BEM results were dominated by yaw misalignment angle, with varying shear exponent and TI leading to more subtle differences. Overall, OLAF results were more consistent than BEM results when compared to SOWFA results under challenging inflow conditions.