Remotely sensed imagery has been used to support forest ecology and management for decades. In modern times, the propagation of high-spatial-resolution image analysis techniques and automated workflows have further strengthened this synergy, leading to the inquiry into more complex, local-scale, ecosystem characteristics. To appropriately inform decisions in forestry ecology and management, the most reliable and efficient methods should be adopted. For this reason, our research compares visual interpretation to digital (automated) processing for forest plot composition and individual tree identification. During this investigation, we qualitatively and quantitatively evaluated the process of classifying species groups within complex, mixed-species forests in New England. This analysis included a comparison of three high-resolution remotely sensed imagery sources: Google Earth, National Agriculture Imagery Program (NAIP) imagery, and unmanned aerial system (UAS) imagery. We discovered that, although the level of detail afforded by the UAS imagery spatial resolution (3.02 cm average pixel size) improved the visual interpretation results (7.87–9.59%), the highest thematic accuracy was still only 54.44% for the generalized composition groups. Our qualitative analysis of the uncertainty for visually interpreting different composition classes revealed the persistence of mislabeled hardwood compositions (including an early successional class) and an inability to consistently differentiate between ‘pure’ and ‘mixed’ stands. The results of digitally classifying the same forest compositions produced a higher level of accuracy for both detecting individual trees (93.9%) and labeling them (59.62–70.48%) using machine learning algorithms including classification and regression trees, random forest, and support vector machines. These results indicate that digital, automated, classification produced an increase in overall accuracy of 16.04% over visual interpretation for generalized forest composition classes. Other studies, which incorporate multitemporal, multispectral, or data fusion approaches provide evidence for further widening this gap. Further refinement of the methods for individual tree detection, delineation, and classification should be developed for structurally and compositionally complex forests to supplement the critical deficiency in local-scale forest information around the world.