The Wide-Field Infrared Transient Explorer (WINTER) is a new 1 deg 2 seeing-limited time-domain survey instrument designed for dedicated near-infrared follow-up of kilonovae from binary neutron star (BNS) and neutron star-black hole mergers. WINTER will observe in the near-infrared Y, J, and short-H bands (0.9-1.7 microns, to J AB = 21 magnitudes) on a dedicated 1-meter telescope at Palomar Observatory. To date, most prompt kilonova follow-up has been in optical wavelengths; however, near-infrared emission fades slower and depends less on geometry and viewing angle than optical emission. We present an end-to-end simulation of a follow-up campaign during the fourth observing run (O4) of the LIGO, Virgo, and KAGRA interferometers, including simulating 625 BNS mergers, their detection in gravitational waves, low-latency and full parameter estimation skymaps, and a suite of kilonova lightcurves from two different model grids. We predict up to five new kilonovae independently discovered by WINTER during O4, given a realistic BNS merger rate. Using a larger grid of kilonova parameters, we find that kilonova emission is ≈2 times longer lived and red kilonovae are detected ≈1.5 times further in the infrared than the optical. For 90% localization areas smaller than 150 (450) deg 2 , WINTER will be sensitive to more than 10% of the kilonova model grid out to 350 (200) Mpc. We develop a generalized toolkit to create an optimal BNS follow-up strategy with any electromagnetic telescope and present WINTER's observing strategy with this framework. This toolkit, all simulated gravitational-wave events, and skymaps are made available for use by the community.