My latest toy to hang antennas up in the tree is a catapult with an old fishing rod, a fishing reel and heavy lead weight attached. The rod splits in two so I have just used the base with the catapult attached via two jubilee clips.
The idea is to fire the catapult over the targeted tree branch thus releasing the fishing line. Once happy with the positioning of the line over a branch, you attach a stronger piece of cord to the weighted end of the fishing line and reel in back over the tree branch. Tie the two cord ends together so that you have a long loop then you can add the antenna to the loop and pull up and down to your hearts content.
I've seen the idea on a couple of web sites and thought I'd give it a go as I wanted to raise the Windom up in my silver birch tree to the maximum height possible, thereby raising it a further 15 odd feet to about 35 feet in total, hopefully this will improve the transmit/receive.
I've done some testing with the catapult in a local field and it seems to work reasonably well getting a distance of roughly 100 feet without really trying. I'll put it to the real test (excuse the pun) over the weekend and we'll see what happens.