In addition to demonstrating the ability of AutoBADDIE to fit IPs, we found that the agreement between DFT-computed and classical IP-computed forces and energies for gasphase clusters of component molecules does not necessarily correlate with accurate solvation and kinetic properties of condensed phase simulations of polymers. Our findings highlight the complexities of using methodical machine learning-based approaches to predict classical IPs due to the limited expressivity of nonpolarizable charge interactions to model chargedependent systems.