We present here some lessons learned from observations and applications of child-robot interaction research in diverse ecosystems such as schools, therapy centers, and hospitals, where the interaction was facilitated in real-world circumstances rather than lab settings. Specifically, we use observational results from our reflections on multiple child-robot interaction practices in the wild conducted over a 9-year research period. Using these exploratory studies, we outline some general design considerations and adaptation guidelines for improving the design and implementation of robotic systems in healthcare and education that might lead to more practical, feasible, and ethically sustainable results.