Not sure why addaline is crashing the box, I will have to look into that.
As mentioned above I would use teamviewer, both of you install it on your computers and then you can connect to his computer from yours and 'take control of it' and do it for him.
He could set up port forwarding on his router so port 21 points to his box and then you could use filezilla to connect to his box but team viewer is safer and easier.