We analyze the absorption and emission-line profiles produced by a set of simple, cool gas wind models motivated by galactic-scale outflow observations. We implement monte carlo radiative transfer techniques that track the propagation of scattered and fluorescent photons to generate 1D spectra and 2D spectral images. We focus on the MgII 2796,28303 doublet and FeII UV1 multiplet at ~2600A, but the results are applicable to other transitions that trace outflows (e.g. NaI, Lya, SiII). By design, the resonance transitions show blue-shifted absorption but one also predicts strong resonance and fine-structure line-emission at roughly the systemic velocity. This line-emission `fills-in the absorption reducing the equivalent width by up to 50%, shift the absorption-lin centroid by tens of km/s, and reduce the effective opacity near systemic. Analysis of cool gas outflows that ignores this line-emission may incorrectly infer that the gas is partially covered, measure asignificantly lower peak optical depth, and/or conclude that gas at systemic velocity is absent. Because the FeII lines are connected by optically-thin transitions to fine-structure levels, their profiles more closely reproduce the intrinsic opacity of the wind. Together these results naturally explain the absorption and emission-line characteristics observed for star-forming galaxies at z<1. We also study a scenario promoted to describe the outflows of z~3 Lyman break galaxies and find prfiles inconsistent with the observations due to scattered photon emission. Although line-emission complicates the analysis of absorption-line profiles, the surface brightness profiles offer a unique means of assessing the morphology and size of galactic-scale winds. Furthermore, the kinematics and line-ratios offer powerful diagnostics of outflows, motivating deep, spatially-extended spectroscopic observations.