Hi,
If you create a new folder from the vLookup interface and add the “connection metadata” to this folder, any documents uploaded to this folder will then be shown in the vLookup parent item as if they had metadata directly on the file.
With this approach you can create the folder from vLookup, and then open the folder in a new window (link from vLookup when hovering over the folder), and upload the documents using the standard SharePoint interface.
Alexander