The arrival of gravitational wave astronomy and a growing number of time-domain-focused observatories are set to lead to an increasing number of detections of short gamma-ray bursts (GRBs) launched with a moderate inclination to Earth. Being nearby events, these are also prime candidates for very long-term follow-up campaigns and very long-baseline interferometry, which has implications for multi-messenger modeling, data analysis, and statistical inference methods applied to these sources. Here, we present a comprehensive modeling update that directly incorporates into afterglowpy astrometric observations of the GRB position, Poissonian statistics for faint sources, and modeling of a trans-relativistic population of electrons. We use the revolutionary event GW170817 to demonstrate the impact of these extensions both for the best-fit physics parameters and model selection methods that assess the statistical significance of additional late-time emission components. By including in our analysis the latest Chandra X-ray observations of GRB 170817A, we find only weak evidence (≲2σ) for a new emission component at late times, which makes for a slightly more natural fit to the centroid evolution and prediction for the external medium density.