We analyze the steady-state transmission of high-momentum (high-k) electromagnetic waves through metal-semiconductor multilayer systems with loss and gain in the near-infrared (NIR). Using a semi-classical optical gain model in conjunction with the scattering matrix method (SMM), we study indium gallium arsenide phosphide (InGaAsP) quantum wells as the active semiconductor, in combination with the metals, aluminum-doped zinc oxide (AZO) and silver (Ag). Under moderate external pumping levels, we find that NIR transmission through Ag/InGaAsP systems may be enhanced by several orders of magnitude relative to the unpumped case, over a large angular and frequency bandwidth. Conversely, transmission enhancement through AZO/InGaAsP systems is orders of magnitude smaller, and has a strong frequency dependence. We discuss the relative importance of Purcell enhancement on our results and validate analytical calculations based on the SMM with numerical finite-difference time domain simulations.