I have recently tried uploading multiple attachments at the same time. Lets say you want to upload a dozen images named Image1 - Image12. If you select all the images then Image12 will import first, then Images 1 through 11 in order. If you then choose to post those images all at once then they will post in their imported order. I recommend modifying the import to not place the last image first. This of course is a very minor issue that most people wont ever notice, but I had to work around it a couple times.
A second issue concerns the placement of the image. If you use the WYSIWYG editor the image will be placed where your cursor pointer is located. If you use the rich text editor the image is always placed at the bottom. Users then need to cut/paste the image to the correct location.
I love the current system. Just some feedback to make it even better.