Does JAMF Pro offer any mechanism to upload files from Mac endpoints to the JSS?
Technically, yes. There is an Attachments section to every Mac record in the Jamf Pro server. And the API has the ability to add those attachments to the records. However, I wouldn't recommend adding very large attachments or multiple attachments to every record as this really adds size to your database and could cause you some problems later, unless you are clearing those out periodically. Small text files, like service records or other simple text/pdf based documents make good attachments. I'm not sure how well it handles zips since I haven't done that, but it should I think.
But keep in mind that if you can script something, then the Jamf Pro server can run it on your endpoints. Some caveats apply here, such as whether some or all of the script needs to be run as the current user and not as root, but that's still doable with the right know-how.
So the answer is, yes, your Jamf server can help with some of this. It might even be able to upload the resulting zips to the analytics server, depending on if you can use something like curl or ftp other tools to do the upload. This would bypass using the Jamf server as the intermediary collection point.
