Hello there Mike,
Are you a ham? Is this for a TV type antenna, HF, or VHF? The reason I ask being a ham myself, I have had an HF antenna strung up in a limb much like the one in the picture. You can use a fishing pole and a sinker to throw over that limb, then tie the sinker end of the fishing line to a rope which has your antenna attached on the other end. You can raise your contraption pulling on the rope, and when you get it high enough, tie the rope off to the tree trunk. That way you have done everything safely on the ground. This method is much like the pros who place their light throwline over a particular limb or crotch, and then pull up their heavier climbing line in a tree.