The last time I had to bore a hole with a brace'n'bit was back when I was a little ol' helper. We had to sink a wood pole in the middle of a lumber yard to raise a triplex that hung too low.
So, here I am on top of two stacks of rough-cut lumber, one on the other, then lifted to the max height of a large fork truck, and then I had to stand up a 28' wood ladder toi reach the top of the pole.
I used a length of NM as a makeshift harness so I could lean back and drill a 1/2" hole through the pole, maybe a foot thick at the top. That only took me about 20 minutes or so.
Then I inserted an eye-bolt, screwed a washer and nut on the back end, and use a come-along to pull the triplex up enough to attach it with the slip type of hanger, the kind with a steel wire loop.
Fun job!