This paper presents the largest known benchmark dataset for road damage assessment and road alignment, and provides 18 baseline models trained on the CRASAR-U-DRIODs dataset’s post-disaster small uncrewed aerial systems (sUAS) imagery from 10 federally declared disasters, addressing three challenges within prior post-disaster road damage assessment datasets. While prior disaster road damage assessment datasets exist, there is no current state of practice, as prior public datasets have either been small-scale or reliant on low-resolution imagery insufficient for detecting phenomena of interest to emergency managers. Further, while machine learning (ML) systems have been developed for this task previously, none are known to have been operationally validated. These limitations are overcome in this work through the labeling of 657.25km of roads according to a 10-class labeling schema, followed by training and deploying ML models during the operational response to Hurricanes Debby and Helene in 2024. Motivated by observed road line misalignment in practice, 9,184 road line adjustments were provided for spatial alignment of a priori road lines, as it was found that when the 18 baseline models are deployed against real-world misaligned road lines, model performance degraded on average by 5.596% Macro IoU. If spatial alignment is not considered, approximately 8% (11km) of adverse conditions on road lines will be labeled incorrectly, with approximately 9% (59km) of road lines misaligned off the actual road. These dynamics are gaps that should be addressed by the ML, CV, and robotics communities to enable more effective and informed decision-making during disasters.