There should be a render function of some sort that can be called that changes how the Uploads are displayed.
In the attached image, I uploaded a single file, then two additional files.
Rather than having a set of one and a set of two, I'd prefer to have either a set of three, or three sets of 1. 

I understand that the plugin creates an input element for each individual uploading, however, I think there would be value in being able to join or split those files into multiple elements. It may even be beneficial to add and utilize a FileList object in the Kendo Upload object, as this would allow for the uploads to be sorted alphabetically, or by type, and so on. 

To recreate the behavior mentioned, simply upload any number of files to an Upload control and then do that one more time. The behavior can be recreated on the Telerik website demos.