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We describe simulations of deep subsurface imaging with low frequency pulsed radar. A FDTD and ray tracing simulation framework is used to model measurements targeting the detection of a wet layer at depths of 350m and below under dry limestone. Loss parameters and wave propagation velocity in limestone were measured in-situ and imported in the simulator. Operating characteristics such as pulse shape and noise levels of the measurement apparatus were obtained from an existing commercial radar scanning system. Results were used to test and optimize data analysis methods, predict maximum detection depth under realistic time constraints, and guide experimental design parameters such as the amount of replications required for denoising and length of the WARR scan lines used for velocity estimation.