In Roller 4 we had the ability to upload multiple (up to 5) files at once. Media blogging does not support this, that's not acceptable and I'd like to fix it. Here is what I propose.
When you choose the Add Media File option, you'll see the same form as we now have but with 5 file upload controls.
Any information that you enter into the form will be applied to all files, except that each file will be named with the pattern <name from the form><sequence number>. So if you upload 3 files with the name foobar, you will end up with files named foobar1, foobar2 and foobar3.
If you upload images then, after you upload, Roller will show you the thumbnails for the files you uploaded and the links. Roller will also give you the option to create a blog entry including one or more of the uploaded images.