>I want to upload a simple comma delimited text file to the server using a browser. Each record in the file contains a field with a full path to a corresponding jpg file. Will I be able to manually upload just the text file and then automate the uploading of each corresponding image file? How could I do this?

Unless you have some sort of pull technology, not relally - the server has no clue about what to do with the path, since it is not it's path. You're going to need to write a file transfer app. I'd recommend building a zip file at the client that contains the JPEGs to upload, and a text file with a constant name telling the server what each file is; there server receives a songle file and has no further need to talk to the client, and the client, who had to create the list, can create the list and prepare the files for transmission as a single step. There's no need of an ongoing conversation, and zipping the data will reduce transmission time and aid in the detection of errors.