The launches of Parker Solar Probe (Parker) and Solar Orbiter (SolO) are enabling a new era of solar wind studies that track the solar wind from its origin at the photosphere, through the corona, to multiple vantage points in the inner heliosphere. A key ingredient for these models is the input photospheric magnetic field map that provides the boundary condition for the coronal portion of many heliospheric models. In this paper, we perform steady-state, data-driven magnetohydrodynamic (MHD) simulations of the solar wind during Carrington rotation 2258 with the Grid GAMERA model. We use the ADAPT and AFT flux transport models and quantitatively assess how well each model matches in situ measurements from Parker, SolO, and Earth. We find that both models reproduce the magnetic field components at Parker quantitatively well. At SolO and Earth, the magnetic field is reproduced relatively well, though not as well as at Parker, and the density is reproduced extremely poorly. The velocity is overpredicted at Parker, but not at SolO or Earth, hinting that the Wang–Sheeley–Arge (WSA) relation, fine-tuned for Earth, misses the deceleration of the solar wind near the Sun. We conclude that AFT performs quantitatively similarly to ADAPT in all cases, and that both models are comparable to a purely WSA heliospheric treatment with no MHD component. Finally, we trace field lines from SolO back to an active region outflow that was observed by Hinode/EIS, and which shows evidence of elevated charge state ratios.