Hi Victoria,
Oh the power of WinDev / Webdev shines!
Here's the solution I came up with. I wrote a Java Applet in WinDev that acts as a "Wizard" like interface. In my case, the applet allows them to select a directory on their local drive that holds the images, documents, spreadsheets and pdfs. When they hit the upload button, not only do I upload everything, I also verify the size of the images and optimize them for the web before uploading. This saves the hassle of people trying to upload the giant images that today's cameras produce.
You could just as easily have the java applet repeatedly do an http post with the image data. The http post would certainly need to authenticate and also pass in a parameter telling the server where to put the the images.
Bottom line is, if you can write in WinDev / WebDev you cna produce a java applet with WinDev to publish with WebDev. Below is a screenshot of the web page with the java applet in it. Once initialized you can't tell where the web page stops and the applet starts.
Cheers!
Ken