It doesn't work that way. If you could see the wear arc before pulling the pin, you would see that it is always centered along the chain, not at an angle to it. Wear occurs on the pins due to a force vector directed along the links, as if trying to pull the chain apart. The pin is fixed in place by the outer plates, so the pin always resists the force on the same side. Flip the chain over and the force vector hasn't changed in relation to the pin. It will still wear on the same surface.
If you could figure out a way to rotate the pins, you could get more wear. Perhaps a pin-orientation modification to the ShelBroCo procedure is the way to go on that.
No. The wear occurs when the link bends over the chainwheel or off the cog, and it's always in the same range. You can clearly see it when you press the pin out. No wear occurs when the chain is straight because there's no movement, and no wear occurs on the derailler pulleys or at the bottom of the chainring or cog because the load is low. Turning the chain over effectively rotates the pins and bushings, and moves the wear surface to a new area of the pin. It nearly doubles the life of the chain. IIRC that was attributed to Shimano engineers a few years ago.
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