try opening the preferences->Bug Reports->View Example and look for the line (about 1/3 of the scroll bar) that says

Received incoming this session: true

If you have been running for a few hours and it says 'false', that means you are still being blocked from uploading your stuff easily.

btw--can you get your videos to your OS 9 friend and see if he can share them?

also, if you go to the Connections Page, and you and your friend both type in each other's IP addresses and port in the box beside the ADD button, you can try to force LW to make a route to each other's files.