Measuring the masses of protoplanetary disks is crucial for understanding their planet-forming potential. Typically, dust masses are derived from (sub-)millimeter flux density measurements plus assumptions for the opacity, temperature, and optical depth of the dust. Here we use radiative transfer models to quantify the validity of these assumptions with the aim of improving the accuracy of disk dust mass measurements. We first carry out a controlled exploration of disk parameter space. We find that the disk temperature is a strong function of disk size, while the optical depth depends on both disk size and dust mass. The millimeter-wavelength spectral index can be significantly shallower than the naive expectation due to a combination of optical depth and deviations from the Rayleigh-Jeans regime. We fit radiative transfer models to the spectral energy distributions (SEDs) of 132 disks in the Taurus-Auriga region using a Markov chain Monte Carlo approach. We used all available data to produce the most complete SEDs used in any extant modeling study. We perform the fitting twice: first with unconstrained disk sizes and again imposing the disk size-brightness relation inferred for sources in Taurus. This constraint generally forces the disks to be smaller, warmer, and more optically thick. From both sets of fits, we find disks to be ~1-5 times more massive than when derived using (sub-)millimeter measurements and common assumptions. With the uncertainties derived from our model fitting, the previously measured dust mass-stellar mass correlation is present in our study but only significant at the 2{sigma} level.