I like to keep the plug wires the way they were from the factory, just for the convienience of some future schmuck who is trying to tune a car. Chevy used the post just clockwise of the points window as #1 for all points distributors, so that's where I leave them. On the HEI they used your #2 view, so I leave them that way on HEI systems as well.
We can change them up and have #1 anywhere, as long as the wires are hooked up in the right order and the rotor is pointing correctly, but it still can cause confusion in the future when somebody replaces plug wires and puts them on in the "normal" position and the engine wont start again. I've seen it happen unfortunately, and it took some time to figure out what was going wrong.