In this work we demonstrate that HF/6-31G* yields a characteristic overpolarization that is in agreement with previous studies, but that this overpolarization is not consistent across all chemical moieties. In particular, for some moieties the overpolarization is >35%, while other moieties are underpolarized relative to the gas phase (i.e., unphysically low dipole moments). In contrast, the combination of a relatively simple hybrid GGA (or meta-GGA) functional, augmented basis set, and implicit solvent yields dipole moments with greater characteristic overpolarization and much greater consistency across all moieties. We then discuss these results in the context of both historical and recent work in the force field development community, as well as their implications for future force field development.