Wordpress has a much simpler task because it generally has one author posting blogs with images, video and sound.
- Moodle needs to manage all kinds of files, including hierarchies of html files or word documents, for example, as well as attachments.
- Moodle has to be able to support the many new types of repositories (with browsing and searching) that we want to support.
- Moodle also needs to work very similarly when Javascript is not available.
- Finally we are trying very hard not to modify core TinyMCE at all (just adding plugins), so that we avoid the forking problems we got into with the old HTMLarea in Moodle 1.x.
For all these reasons the filepicker part where you choose a file to use is separate from the settings and preferences about where the file actually ends up. So I can't see the filepicker that we currently have in 2.0 changing much in functionality, we just need to fit it all together in the best way.
However, I do agree with the priority list and your sidenotes.
And yes, I totally agree that good data would be very useful, unfortunately it looks like we need to create some draft solution first so that people can understand the full extent of the issue in practice.
Still thinking...