I gotta tell you, this is what bittorent was invented for.
Download Azureus
Install it.
Click "File"
"New Torrent"
"Next"
"Browse" to the file you want to send.
"Next"
"Finish"
Click teh torrent you've made. Copy the tracker link (which is your IP and port) that's listed, and paste it to your buddy/whatever via IM or an email. Bang, they click teh link, see your tracker, start downloading.
It's really not much more complex than that.
Of course, the reciever would need to have a torrent client too. And you said not major computer skillz on the other end. But maybe you can use this elsewhere.
Decent how to guide.