Have you set both connectionTimeout and connectionUploadTimeout to a large time period in the Tomcat server.xml file?
-Mike
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I'm not very familiar with your proxy configuration so I don't know what might be going wrong with that (I'm assuming the files you're trying to upload are significantly less than 4gb).
If you go with the upload assistant route, is there a reason you couldn't set the prearchive settings in the projects your users are uploading to so that the data ends up in the prearchive? The setting is under the 'Manage' tab at the top of the project page in the 'Define Prearchive Settings' section.
-Mike