It is indeed possible to add a folder to and App's File Sharing space using iTunes version 12+. However, the iTunes upload button will not work for this, because its file selection interface insists on plain file selection only, excluding folders. The way which works is to drag-and-drop a folder from your PC to the iTunes File Sharing window.
Since the iTunes interface for handling file sharing is very poorly designed, is is worth recalling the tricks that you can use to perform operations on the File Sharing space, that iTunes does not provide a button for:
- Rename a file or folder: click it once, wait for a couple of seconds, and click it again. This will replace the name with the renaming edit box
- Delete a file or folder: select it, then hit the "Del" key on your keyboard
- Upload a folder: drag-and-drop it from your computer copy
It remains impossible to directly see or alter the contents of a File Sharing folder in iTunes. My workaround for doing this is the following:
- Download the folder to the computer
- Make any desired change to the folder tree on the computer copy
- Delete the File Sharing copy of the folder (or, optionally, rename it to something like folder.old for safety)
- Upload the modified folder from the computer, using drag-and-drop
- (optionally) Delete the safety copy in File Sharing, after verifying that the App works fine with the newly uploaded version of the folder
I hope this helps