Great plugin, will have it live soon.
Quibbles/bugs/suggestions:
1. The file icon is linked to the actual icon gif - should ideally be a css background, or at least an unlinked image.
2. Image files do not open in the browser, but rather are downloaded? Ideally using Highslide would be preferable, but would it not at least be possible to have the image open in a new window? Having it behave more like a normal image (so you could right click save as) would be more intuitive for users.
3. Perhaps something for the future: maybe we could have the autoinserts generated with some alt/title text - perhaps just grabbed from the thread title or similar, or user entered (probably not).
4. I'm afraid I haven't tested this, but is it safe to use multibyte characters (I'm especially concerned with East Asian character support personally) in filenames and so forth? Will it fail gracefully if not?