Converting traditional knowledge base into in-app context relevant articles

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I want to organize KB articles so they are directly accessible from relevant menus in our cloud based web application. I imagine something like "related articles" as typical from Wiki based KB platforms. I need to find a good structure for linking the web-app and doc-repo and to keep things in sync. I wonder if someone here have some good experience to share around readthedocs.

I debate with myself different approaches:

  1. Simply have unique URLs for each relevant doc. This requires that the URLs are manually applied to each web-app section. When the doc is updated, then it must maintain the same URL. The problem here is, if a tech writer wants to apply another relevant article, then the web-app must be updated. A maybe not so urgent issue is that some docs may be web-app version specific, i.e. one version applies to Web-app v2.0, others to Web-app v3.0 and then some that are generic.
  2. As above, but link to a folder with relevant docs., so the tech writer just drops the relevant docs in the folder. The problem here is that you will get duplicate documents, as some may apply to different web-app sections.
  3. Apply tags to each doc, where the tag indicates the web-app section where this "related article" should be linked to, e.g. "User Management". Somehow the Web-app should be able to retrieve links to relevant docs based on the tag.

There may be other and better methods, and surely I want to automate the flows as much as possible. I know that assuring that UX related code changes are automatically reflected in related articles would be quite a large job, so it is primarily just assurance that nothing breaks and avoiding dead links.

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