I'm not sure about the functionality of that ansible-playbook and the local-configure.yml file. Does this require merging, deployment, reload or the like?
IMO, for documentation we should have something much more agile.
Zope allows to traverse the subpath. Why not have Python methods which do so, and check for matches in a relational table?
E.g., we could have a
documentation script, living in the root of https://plone.org, which of course knows about its name, and checks the table for an exact match for
documentation and the subpath. If there is such a match, a redirection to the new location is performed (Plone 4 version, I'd say, because those old pages will almost certainly refer to Plone 4 or earlier). If there is no such exact match, (after a little "sorry" message) a form could be presented where the user can suggest a redirection target; administrators can view those targets and choose the best one.
Redirections which swallow path information (like
/download) are evil and should be removed. They are worse than nothing.