Acquiring data across many locations and enabling fast decision-making are strengths of hyperspectral measurements. Nevertheless, a range of data processing approaches (Savisky-Golay [SG], first derivative [FD], and normalization) and modeling frameworks (partial least squares regression [PLS], weighted k-nearest neighbor [KKNN], support vector machine [SVM], and random forest [RF]) can be applied to establish the strongest link between physical observations and hyperspectral signatures. In this study, FD emerged as the top processing technique, while SVM was the leading model for estimating mean cotton (Gossypium spp., Malvaceae) height and node counts. Conversely, the integration of FD with RF achieved the highest accuracy in predicting cotton leaf area index, canopy cover, and chlorophyll levels throughout the growing period. Furthermore, outputs from models built with both SVM and RF corresponded closely to the pseudo-CHIME satellite wavebands, a process in which field-collected hyperspectral data were adjusted to the spectral intervals of an anticipated spaceborne hyperspectral sensor. The knowledge and outcomes supplied here will equip growers and other players in the cotton sector to execute swift, well-informed actions that could foster higher productivity and sustainable intensification.