From another drupal.stackexchange answer, this module called Filebrowser looks like an ideal solution (I've yet to test) for discrete folder listing of files. From the Filebrowser project page:
You will create one node (node type dir_listing) for each each
Directory Listing (DL). Node settings are used to control access and
other features of the DL. These settings can vary per node and per
user.
This module offers the following features:
Private downloads so that files (such as PHP files) can be downloaded.
File blacklists so that specific files can be removed from directory
listings. Node-based. All features available to nodes, such as path
aliasing and access control can be applied to directory listings.
Settings to limit exploration of subdirectories
The latest Filebrowser version 7.x-4.0-rc1 can do multiple file uploads (drag and drop) if the Plupload module along with the Plupload library dependency (ie extract zip file into library folder at sites/all/libraries/plupload) are available. Looks like it offers file meta-information options as well.

The .info file for Filebrowser does not have a Views dependency so it is likely Views contextual filters or Views relationships needs tweaking, or alternately some type of views enhancement module such as the popular EVA - Entity Views Attachment, or block or entity reference module possibly with Context module, could be needed to solve the display/view/layout in cases like this question. Also, depending on the roles/permissions that Filebrowser does, or may not have, coded into this module with its content type, ACL (Access Control Lists) with Content Access might be additional modules for privacy of the custom file listings/nodes.
Kudos to the community developers for this module, that is showing active development activity at the time of this answer. Try to contribute back folks!