At my first job we were in a similar position I think with lots of churn (volunteers, young people).
I argued with my boss and finally got a vm with a MediaWiki instance. I created a simple frontend using Javascript and html to simplify correct addition of common page types.
Obstacles: my boss and certain other people wanted something more businessy. Also they wanted to run the DB on MSSQL, while MediaWiki is supposed to use MySql I think.
At a later place I was tasked with moving/updating documentation from a two page Word document to a Confluence document. It was written by a long time developer so it grew quite a lot.
Obstacles: Confluence :-] Also getting people to admit when their previous docs are wrong (or at least deviates from official vendor docs, and it creates problems.) Also trying to keep it up to date while others are constantly changing things.
Later on I've
- used OneNote,
- got others to use OneNote
- failed to get people to use OneNote,
- updated Confluence plug-ins,
- struggled with people who said they used README-driven development, but were really just their personal notes on what they'd need to remember.
Finally there are some common theme:
- refusing to acknowledge the need for any system beyond mail and Word documents.
- insisting on buying one lf the "commercially supported" but otherwise inferior and close to unusable system
- insisting on using SharePoint (a variation of the point above)
- putting everything into Confluence which means hopeless search + access restrictions so you never know if 1) the document exists but you don't have access, 2) it exists but you cannot find it because it is in the wrong place and search is broken 3) the document doesn't exist.