Automating API documentation is crucial for ensuring it remains accurate and user-friendly, as outdated documentation can frustrate users when it doesn't match the implementation. The blog, based on a talk from ReadMe's API Mixtape conference, emphasizes automating documentation through tools like Swagger/OAS specifications, which can be auto-generated based on code to remain current and accessible. Additionally, it highlights the importance of providing regular, use-case-focused documentation to guide users effectively, suggesting a hybrid approach where some documents are maintained within the codebase while others are edited externally. Personalization is also key, with tools like ReadMe allowing integration of API keys directly into the documentation to lower the entry barrier for users and creating personalized user experiences through automated logins. Overall, automating documentation not only keeps it up-to-date but also enhances user satisfaction by making it more interactive and accessible.