Laureen --
After I sent my reply, it dawned on me maybe you were talking about
uploading documents to SharePoint subwebs. Yes, what your user wants to do
can be done. Here's how:
1. Navigate to the Documents library the project workspace.
2. Click the New Folder button
3. Create a WSS folder that matches the first folder of the documents he
wishes to upload and then click the Save and Close button.
4. Click the Upload Document button.
5. Click the "Upload Multiple Files" link.
6. Navigate to the folder containing the first set of documents.
7. Select the checkbox beside each document he wishes to upload from that
folder.
8. Click the Save and Close button.
9. Repeat steps 2-8 for every folder containing documents he wishes to
upload.
Hope this helps.