Sooooo, this is a little overdue. But I've finally managed to get multiple photo/file upload installed.
Now, when you go to the "Upload attachment" tab while posting, you'll note a little plus sign next to the Filename field. Just click that plus, and another set of Filename and File comment fields will pop up. You can keep clicking and adding more. Fill everything in, click "Add the file," and all of the photos/files will be uploaded all at once.
I'm not sure if there's a cap on this, but uh... please don't go out of your way to try to break it
As usual, if anybody notes any issues, respond here or drop me a line.