WordPress covers everything I could want for blogging almost perfectly, except for the media management.
There are a couple of improvements I'd like to see happen to the media library for it to be the perfect tool for me.
1) The ability to retroactively scan for images attached to posts:
Every once in a while, my images do not get linked to the posts when I upload them. Additionally, I have a lot of files in my media library that were uploaded back when the media library was very new, and they seem to have been "unlinked" to the posts. On the blog front-end, everything appears fine, but on the back-end, it's very sloppy. The potential for organizing with the media library is great, but it needs to be able to be made aware of what's linking to what, and be able to re-link orphaned attachments.
2) The ability to upload large files, automatically resize them, and then delete the original:
The image uploader is amazing. I love that I can upload a large file and it automatically resizes it to fit my set sizes. However, if I upload large digital photographs (3000 pixels or more), I have no need for the original file to be saved on my blog -- just the resized versions. Resizing the photo manually before uploading it defeats the entire purpose of WordPress's auto resize setting. I'd like to see an option to upload the large file, resize it, and then delete the no-longer-necessary large file.
Anyway, you guys are doing a great job on development. I love everything you've done so far. I hope that my suggestions will make it into a future version of the Media Library.