Well we are in the process of moving (or trying to move) a large Wordpress community to Discourse, so there is alot of functionality with uploads (and other things) we are trying to accomplish, as our community is very image intensive.
For example, the Topic List Previews plugin is amazing, but it only allows you to choose topic list previews from images at are already associated with a topic or its posts. But what if you want to use an image that already has been uploaded to another topic as the preview? You can’t do that easily. What if an admin wants to insert an image into a topic from an image that has already been uploaded to another topic? You can’t do that either easily, without going to the data explorer and getting the URL and pasting back into the editor (as the editor doesn’t allow you choose an image from the already uploaded images). Also, occassionally admins need to edit uploaded images for various reasons, but there is no easy way to do that either. These are just a few of the issues. For now we can work around it, but over time I guess we’ll program some things to make the management easier and provide more functionality.