Hello John S.,
Yes, this can be achieved - can you please take a look at the functionality offered by our Jobs module included in the Sitefinity SDK which does exactly that - it offers a frontend UI allowing users to select a document from their filesystem and then it gets uploaded to a specific library. You can then put a Download list widget and set it to display the documents from that library. For more information about the implementation of Jobs module, please check the SDK and this tutorial
from our Documentation.
I hope you find the above information useful. If you have any additional questions, please let us know.
the Telerik team
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