Just as there is no such thing as absolute security, there is no such thing as a 100% intuitive and self-documenting UX.
No matter how simple or complex software is, there is a limit to how much "help" the UX can offer. The UX should have enough hints/labels/tooltips/etc to keep the user from getting lost performing light to medium tasks, but inline is not the place for describing complex workflows, data structures, APIs, or other heavy topics.
Documentation is the ultimate resource for the users, most documenting elements in the UX should be considered a convenience. The phrase "RTFM" exists for a reason, there is no "RTFUX".
It also sounds like you're handling your docs wrong... they should evolve with the codebase and not need a complete rewrite for every release.