you need to use technology that bypasses the browser security model .: - (
Javascript running in the browser does not have access to the file system for security reasons and likewise has very limited access to the file upload control. (for example, you do not want the browser to be able to safely upload files to a remote server)
A very popular open source project that allows you to bypass the SWF Upload security model to some extent. Unfortunately, out of the box, this does not allow you to do what you want, to create renewable downloads. This means that you have to either hack it (it's open source) or use another technology that is more convenient for you, for example, Java or a browser extension.
EDIT:
A new jQuery plugin has been announced that will help you exactly what you want. It was called plupload: http://plupload.com/
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