cPanel: there were like 3 different APIs if I recall, and most people had to use API v1 and API v2 together. Neither was feature complete or bug free enough to use independently and it was an insane amount of trial-and-error to figure it all out.
Old PayPal APIs: while generally not many APIs are required, figuring out what ones to use was horribly painful.
Google Workspace: even though our company was large and had account reps to help, sorting through their horribly written documentation and figuring out the APIs was a shocking nightmare. You couldn't help but compare to this to the earlier days of Stripe: awesome docs, great API design, trivial to get sandbox accounts, responsive and knowledgable free support.
Too of often I think these APIs were written by people who had no good fundamentals on what the complimentary side of development life is like as a consumer of the API. Happy to grant that these people were rockstars at solving other problems... but this was NOT strong point.
Even what should be trivially easy (e.g. did the request succeed or not?) required parsing API-specific responses. And if it failed, good luck trying to know why and whether anything could be reasonable shown to an end-user.