The goal of the OSIRIS-REx mission is to return a sample of asteroid material from Near-Earth Asteroid (101955) Bennu. The role of the navigation and flight dynamics team is critical for the spacecraft to execute a precisely planned sampling maneuver over a specifically-selected landing site. In particular, the orientation of Bennu needs to be recovered with good accuracy during orbital operations to contribute as small an error as possible to the landing error budget. Although Bennu is well characterized from Earth-based radar observations, its orientation dynamics are not sufficiently known to exclude the presence of a small wobble. To better understand this contingency and evaluate how well the orientation can be recovered in the presence of a large 1$^{circ}$ wobble, we conduct a comprehensive simulation with the NASA GSFC GEODYN orbit determination and geodetic parameter estimation software. We describe the dynamic orientation modeling implemented in GEODYN in support of OSIRIS-REx operations, and show how both altimetry and imagery data can be used as either undifferenced (landmark, direct altimetry) or differenced (image crossover, altimetry crossover) measurements. We find that these two different types of data contribute differently to the recovery of instrument pointing or planetary orientation. When upweighted, the absolute measurements help reduce the geolocation errors, despite poorer astrometric (inertial) performance. We find that with no wobble present, all the geolocation requirements are met. While the presence of a large wobble is detrimental, the recovery is still reliable thanks to the combined use of altimetry and imagery data.