I would suggest adding the use of Doxygen to your projects. It supports Markdown files as well as Markdown syntax in your code comments. You might find that a lot of what you are documenting in the separate .md files could be a notes or remarks section of your method class comments. This will remove the separation of technical documentation vs. help/FAQ comments by doing all of the documentation in the code. You can then add Doxygen to your build, so that building the project refreshes the documentation. Doxygen can be configured to produce a online html version that can be deployed to an internal web server for quick reference. It can also build .pdf, rich text documents, and unix man pages.
Then if you use Continuous integration/deployment, when you deploy to test, UAT, then eventually production you deploy the official documentation that was generated.
The challenge with all documentation, is, Actually doing it. So it should be part of your SDLC documentation and process. the project/task/request is not done until documentation updated. Make it a checklist item that needs to be reviewed in code reviews. Doing the technical and help/FAQ all in code comments makes that easy.
cheers!