Jim's mission

Your mission Jim...
I have my pole painted and ready. Here it is, laid out. The two horns at the bottom each have rectangular plates with holes at each of the four corners. There are eight holes drilled at the appropriate points in the blue pillar against which the ladder is leaning. I am sure there would be a problem hoiking that pole straight up the ladder and trying to hold it in place, it is just too heavy. Even with someone standing on the roof holding it steady it would be far too dangerous. I think it probably weighs more than 50kg and it is 3 or 4 meters long, so cumbersome to say the least.
These photos are terrible, but if you were the one faced with the problem how you would tackle it?
I think I will need one additional 2x4 and my trusty assistant to either put the bolts in or take the strain for a minute or two as well as help lifting the thing up onto the roof. No other aids.


The lower photo shows another view and you can also vaguely see the blue cable that comes too near to the blue roof, that will be replaced and raised by the pole. Anyway, just another little distraction to contemplate.