The development of diffuse optical tomography (DOT) instrumentation for neuroimaging of humans is challenging due to the large size and the geometry of the head and the desire to distinguish signals at different depths. One approach to this problem is to use dense imaging arrays that incorporate measurements at different source-detector distances. We previously developed a high-density DOT system that is able to obtain retinotopic measurements in agreement with functional magnetic resonance imaging and positron emission tomography. Further extension of high-density DOT neuroimaging necessitates a thorough study of the measurement and imaging sensitivity that incorporates the complex geometry of the head--including the head curvature and layered tissue structure. We present numerical simulations using a finite element model of the adult head to study the sensitivity of the measured signal as a function of the imaging array and data sampling strategy. Specifically, we quantify the imaging sensitivity available within the brain (including depths beyond superficial cortical gyri) as a function of increasing the maximum source-detector separation included in the data. Through the use of depth related sensitivity analysis, it is shown that for a rectangular grid [with 1.3 cm first nearest neighbor (NN) spacing], second NN measurements are sufficient to record absorption changes along the surface of the brain's cortical gyri (brain tissue depth <5 mm). The use of fourth and fifth NN measurements would permit imaging down into the cortical sulci (brain tissue depth >15 mm).