Roads are among the most essential components of any country's infrastructure. By facilitating the movement and exchange of people, ideas, and goods, they support economic and cultural activity both within and across local and international borders. A comprehensive, up-to-date mapping of the geographical distribution of roads and their quality thus has the potential to act as an indicator for broader economic development. Such an indicator has a variety of high-impact applications, particularly in the planning of rural development projects where up-to-date infrastructure information is not available. This work investigates the viability of high resolution satellite imagery and crowd-sourced resources like OpenStreetMap in the construction of such a mapping. We experiment with state-of-the-art deep learning methods to explore the utility of OpenStreetMap data in road classification and segmentation tasks. We also compare the performance of models in different mask occlusion scenarios as well as out-of-country domains. Our comparison raises important pitfalls to consider in image-based infrastructure classification tasks, and shows the need for local training data specific to regions of interest for reliable performance.