I tried tar'ing up my images directory from the server, and unpacking them in a few locations on the filesystem that looked like likely places, but that didn't work. The filesystem layout was kinda confusing with the "user" and "wiki" separation.
How would one prepare a similar image database for an unsupported wiki? I expect this is a custom thing you prepared as opposed to the xml text dump which is a standard mediawiki dump format.
As to the imagemagik part, it doesn't work for an unsupported wiki. Also, it would be impractical for me to manually crawl my whole site triggering downloads of images, and even if I did that, it is unclear how to package and deploy it. The deployment needs to be completely offline becuase there is no Internet at the prison.
Overall, setting up one of the well known wikis is probably pretty smooth, but the private wiki requires a lot of technical knowledge about implementation details that make this tool impractical for unskilled users. Right now, kiwix deployment it is close to ideal. I just need to instruct the unskilled user to replace the ZIM file.
There is one small deficiency in the kiwix deployment in that the automatic index files are user specific unless prepared in advance and recorded in the libary.xml file, so in practice I had to prepare a script to make sure the index and library were right. The actual deployment is "copy zim files to this dir, then double-click on this script"