I think it should look alot like this:
http://www.plone4artists.com/
to see the Jupload drag and dropper just register here
http://www.plone4artists.com/join_form
and login
that is so powerful, to be able to drag and drop and make nodes is ideal.
this is the only way i will get my end users to post content. i mean lots of photos.. lots of media!
this could be integrated with your module and cck in the following way...
the jupload could be a field type with the option to allow each file to become a seperate node or as many attachments of a singe node ...
Categorization:
for categorization there could be a drop down select or a freetagging box could be allowed for either each file/node or all files/nodes at once... brilliant!
Related Nodes:
the uploaded files could make nodes that are simply RELATED to the parent node like children.... example... content type is an album.... you drag and drop the mp3's..... they make children nodes which are of the type "song".. you can then edit them and upload the samples you used in that song... they become children of the content type "sample".....
Allow a "create a child node of the following content type"
another useful field type.. ... someone can chose the samples and/or songs they sampled and simply click a link to create another node of the content type... "remix".. would appear as a link at the teaser or footer "create a remix" ...