This study aims to explore the complexities of digital accessibility, focusing on the essential tasks of evaluating and monitoring the accessibility of digital content. It seeks to identify the main challenges encountered by practitioners on the field and to reveal best practices and research opportunities for enhancing digital accessibility. Using a mixed-methods approach, the study combines an online survey and in-depth interviews, gathering insights from 27 practitioners across 16 countries. The findings underscore substantial gaps in education and professional training within accessibility. Challenges identified include ensuring technical compliance while addressing user needs, limitations of current automated tools, especially for mobile accessibility, and the disparity between formal compliance and user-centric accessibility. The study highlights best practices such as comprehensive training, effective project management, and innovative testing strategies. This research underscores the need for refined evaluation methodologies and a deeper understanding of accessibility principles among stakeholders. It advocates for collaborative efforts to address the nuanced challenges of making digital spaces universally accessible. Future research should leverage emerging technologies, particularly Artificial Intelligence, to enhance accessibility evaluations and bridge the gap between technical compliance and user experience.