Concrete surface cracks serve as early indicators of potential structural threats. Visual inspection, a commonly used and versatile concrete condition assessment technique, is employed to assess concrete degradation by observing signs of damage on the surface level. However, the method tends to be qualitative and needs to be more comprehensive in providing accurate information regarding the extent of damage and its evolution, notwithstanding its time-consuming and environment-sensitive nature. As such, the integration of image analysis techniques with artificial intelligence (AI) has been increasingly proven efficient as a tool to capture damage signs on concrete surfaces. However, to improve the performance of automated crack detection, it is imperative to intensively train a machine learning model, and questions remain regarding the required image quality and image collection methodology needed to ensure the model’s accuracy and reliability in damage quantitative analysis. This study aims to establish a procedure for image acquisition and processing through the application of an image-based measurement approach to explore the capabilities of concrete surface damage diagnosis. Digitizing crack intensity measurements were found to be feasible; however, larger datasets are required. Due to the anisotropic behavior of the damage, the model’s ability to capture crack directionality was developed, presenting no statistically significant differences between the observed and predicted values used in this study with correlation coefficients of 0.79 and 0.82.