Recent determination of the Hubble constant via Cepheid-calibrated supernovae by \citet{riess_2.4_2016} (R16) find $\sim 3\sigma$ tension with inferences based on cosmic microwave background temperature and polarization measurements from $Planck$. This tension could be an indication of inadequacies in the concordance $\Lambda$CDM model. Here we investigate the possibility that the discrepancy could instead be due to systematic bias or uncertainty in the Cepheid calibration step of the distance ladder measurement by R16. We consider variations in total-to-selective extinction of Cepheid flux as a function of line-of-sight, hidden structure in the period-luminosity relationship, and potentially different intrinsic color distributions of Cepheids as a function of host galaxy. Considering all potential sources of error, our final determination of $H_0 = 73.3 \pm 1.7~{\rm km/s/Mpc}$ (not including systematic errors from the treatment of geometric distances or Type Ia Supernovae) shows remarkable robustness and agreement with R16. We conclude systematics from the modeling of Cepheid photometry, including Cepheid selection criteria, cannot explain the observed tension between Cepheid-variable and CMB-based inferences of the Hubble constant. Considering a `model-independent' approach to relating Cepheids in galaxies with known distances to Cepheids in galaxies hosting a Type Ia supernova and finding agreement with the R16 result, we conclude no generalization of the model relating anchor and host Cepheid magnitude measurements can introduce significant bias in the $H_0$ inference.