While the generating &amp; updating of documentation and pushing to a server may be &quot;too technical&quot; MkDocs makes it pretty easy to deploy to Github Pages or generate the HTML to a static directory that can be deployed to a private location.<p>You could have a simple git hook that looks for new commits and re-publish HTML files and then deploy those with something like Deploybot (<a href="http:&#x2F;&#x2F;deploybot.com&#x2F;" rel="nofollow">http:&#x2F;&#x2F;deploybot.com&#x2F;</a>).<p>In terms of authoring the content it&#x27;s simple Markdown formatting, pretty simple to get the hang of. However, it lacks the file upload functionality you&#x27;re asking for.