I have two dozen iPads that I need to somehow get 25 videos files and a half a dozen PDFs loaded into. The devices are in DEP and are enrolled wirelessly. How would I go about getting the media to sync to the iPads automatically? The other catch is that they do need to be available offline as these are going to an area with no wifi and no cellular once they are ready. I'd like to do this without touching them in, but I realize that might not be possible.
For PDF files we host them on an internal web server then push them our to iPads as an in-house ebook within Jamf (will then be available offline on the iPad just use the web-server to host the files to go out)
One thing to note is that unlike with apps to push ebooks in this way the iPad needs an apple id on it.
Not done anything with videos so can't help there.
It can be done with Automator and Configurator 2 (if you aren't able to get the Supervision certificate your JSS is using, this might be more difficult.)
Here's a video from WWDC 2015 on the basic idea: https://developer.apple.com/videos/play/wwdc2015-306/?time=2364 (you'll have to watch it in Safari).
The stock Movies app isn't a thing anymore, but I was able to get videos loaded to VLC using its bundle identifier. Going directly to the Photos app doesn't work (likely due to the way iOS prompts for permissions when other apps try to access the photo roll), but if you make iMovie your destination, they'll go to the "Videos" section—if something like a class video editing project was the goal.