This paper presents the first comprehensive, rigorous, and reproducible study of the Remotely Supervised Estimation (RME) problem using real data. Unlike previous studies that rely on synthetic data, we use real data to assess the feasibility of RME (C1), analyze key phenomena and tradeoffs associated with RME (C2), and evaluate various estimators based on real data (C3). Specifically, we demonstrate that the performance gains of existing deep estimators may not compensate for their complexity and propose simple improvements to address this issue (C4). By making the extensive data collected and the developed simulator public, we bring RME one step closer to practical deployment.