freejuiceIf you say to yourself you're pushing it - then you probably are. I don't think a 20' gin pole is enough to operate safely, and since you don't know heavy everything is, you don't know how much load is required. Have you tried to figure it out?
I believe it was a Ford pickup involved in one tower-raising incident that went badly when the weight of the tower drew the truck, with the brakes on, right up to the anchor base. Well, it could have been any truck, but it's the traction not the engine torque that gets the tower raised.
Youmanskids: I saw your video for the first time. Did you really have two guys standing at the back guy anchor? Do you know how many milliseconds they have to get out of the way if your tow cable lets go?
A sufficiently long gin pole, some freedom of motion in the gin stay wires, adequate safety margins on cables and connections, all (and much more) are necessary if you're going to do this safely.
PS, take that ladder down. When the gin pole for the tower gets long enough that it's hard to access, use a secondary gin pole to lower the main gin pole. Then you can make the connections on it at your leisure, raise it back up, remove the secondary gin pole, and re-attach the tower to raise it.