My biggest two issues:
1) Stripe docs are inaccurate. They frequently don't work exactly as they describe for given subscription workflows. Sometimes an API call is entirely wrong, sometimes it doesn't return the data the docs indicate, and sometimes the arguments it describes just doesn't exist. (Yes, I've ensured I'm using the latest API version in use).
2) The docs have no changelog. There's an API changelog that indicates when API's change, there's nothing indicating when entire chunks of the documentation change on the website, along with the recommended way to integrate. The most obvious example of this is that the subscription workflow docs got a huge makeover in the past year (sometime), with some really great flowchart diagrams. But back to point #1, some of the API calls listed here are not actually valid. If I've just missed the changelog for the website docs, please point me in the right direction. :)
For reference, I'm using Node at the moment, but I've also integrated with Python, and there were breaker bugs in those docs as well. I eventually end up reading the HTTP API docs, then going through the SDK's to see where they went wrong, or the docs went wrong.