Vision- and hearing-threatening diseases cause preventable disability, especially in resource-constrained settings(RCS) with few specialists and limited screening setup. Large scale AI-assisted screening and telehealth has potential to expand early detection, but practical deployment is challenging in paper-based workflows and limited documented field experience exist to build upon. We provide insights on challenges and ways forward in development to adoption of scalable AI-assisted Telehealth and screening in such settings. Specifically, we find that iterative, interdisciplinary collaboration through early prototyping, shadow deployment and continuous feedback is important to build shared understanding as well as reduce usability hurdles when transitioning from paper-based to AI-ready workflows. We find public datasets and AI models highly useful despite poor performance due to domain shift. In addition, we find the need for automated AI-based image quality check to capture gradable images for robust screening in high-volume camps. Our field learning stress the importance of treating AI development and workflow digitization as an end-to-end, iterative co-design process. By documenting these practical challenges and lessons learned, we aim to address the gap in contextual, actionable field knowledge for building real-world AI-assisted telehealth and mass-screening programs in RCS.