If the media is more than 20-30gigs the most efficient workflow is to ship a drive to the editor.
Working with an editor remotely should be a pretty straightforward thing. And if you need to collaborate during the edit I'd recommend using Skype because of Skype's ability to share a screen. I recently worked with a remote producer through skype and it worked well. She and I could talk through our edit and she could watch whatever I selected on the timeline or in the source window.
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