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I used to install towers when I was younger. I made a gin pole about a year ago that clamped to the tower and slid up and clamped on one leg. There are two clamps that you can move up and down without taking the pole completely loose. My pole is made from electrical conduit, and is not as heavy. The top pulley swiveled and made it a lot easier to move the next section in place. Your idea is fine and seems to be able to work well.
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