Symphony.

I'd like to give users the ability to upload multiple files (namely image files, jpg/tiff) at the same time and also display a progress indicator as users may be uploading files large enough to require that they sit and, patiently of course, wait for the upload(s) to complete.

Any help would be appreciated!

SWFUpload might be of use to you. You could have an entry with three upload fields and use SWFUpload to allow uploading of three files.