Can I use iPhoneBrowser to upload a directory structure to Office Connect?
My suggestion would be to get DataViz's Documents To Go. It provides the capability of editing Word documents on your iOS device and the 'premium' version interfaces with Dropbox (or similar services) to synchronize the changes to and from your PC. I haven't personally used their iOS version, but I did use their Palm version several years ago and it worked quite well.


  Microsoft Word Editing
  
  View, edit and create Microsoft Word documents on the go and experience the freedom of being able to review and update any of the Word documents you rely upon; anytime, anywhere. Advanced viewing and editing features include touch navigation, cut/copy/paste, bulleted and numbered lists, fonts, embedded pictures, tables, word count, password-protected files and the ability to edit in landscape view.
  
  Online/Cloud Documents Support
  
  ('Documents To Go Premium' only)
  Download, view and edit your files from your Google Docs, Box.net, Dropbox, MobileMe iDisk or SugarSync account directly in Docs To Go. Any changes you make can be saved and synchronized back to the online account so that you'll always have the most up-to-date version. You can even create new files in Docs To Go and upload them immediately to your account.