On the one hand, its about as easy as it could possibly get.
On the other hand, it involves a middleman so you have to upload and then download (essentially doubling the time it takes) AND its not secure in any way.
There should be a simple file transfer client that doesn't require usernames. Two people have the software downloaded/installed. When you run the program it you are given a text box and an ID string, a random string of digits (different every time, approximately 9 characters long). The two people trade those ID strings, entering the other person's string into the text box. Upon hitting "connect" a server somewhere, (not sure who would run this for free, maybe google), would facilitate the secure connection between both parties. It would be great if it were a SSL connection. Once secure its like a very simplified chat client with the ability to drag & drop files. Chat would allow for verifying, "Hey is this Mike?" "Yeah, is this Kevin?" "Okay send me the video of your girls playing soccer."
I'd call it SECHAFT. SEure CHat And File Transfer. Okay, I know the name sucks, but it needs a name. Someone do one better please
Anyway, yeah, secure, quick and easy, maybe a buddy list but now we're venturing into AIM territory.. i like the 10 digit string idea. You call each other up, trade strings, and send files.