This paper presents insights from the iterative design and evaluation of AuthELO, an authoring tool aimed at augmenting learning tools through adaptable, automated support. By scaling its use in a large EU project, we gained critical insights into the challenges and opportunities following a qualitative, user-centered approach integrating the insights of EdTech experts and teachers. AuthELO was formally evaluated in two design cycles: the first through a workshop with EdTech experts, using a task-based questionnaire, and the second with teachers, who used the tool to develop automated support for an activity. Data collection included observational notes, reflective narratives, and discussion transcripts, providing a rich qualitative understanding of usability and workflow alignment. The findings demonstrated notable improvements in usability and user experience, highlighting the importance of a clear workflow aligned with well-established authoring models that lower the expertise threshold required for engagement.