You can use Digital File Pro for uploading as many images as you'd like, but you would have to apply it one time for each file field on your page.
It would even be possible to upload multiple files from a "single" file field by dynamically creating new file fields using JavaScript, and then you could loop over the available file fields and run the DFP code on each file. But all that's not built in, you'd need to code the filed creation and the looping yourself.