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They'd have to crane each line up and over the towers, sounds difficult. They'd need to put the lines on pulleys hanging off each insulator and fine some way of controlling the slack between towers as they lift the line over.

It is, but surely they have procedures for that such as insulated suits and grounding wires on the new lines, so they don't get energized by static or induction. They might have a switching mechanism or remote controlled tool for the final hookup. Maybe your friend can keep an eye out and take...

Maybe they put up new lines, connect them in parallel to the old, then disconnect and remove the old lines.