I use a slingshot with an open face reel attached to it, drape the wire out in front a bit to avoid snags. I use a 2 oz round fishing weight with some high strength braided fishing line. Managed to get lines up 80-90ft over a limb, attached 550 cord to the weighted side and reeled it back up and over. Works like a charm, If I was closer i'd sure give you a hand.
Pulley is easy to send up, once you have your 550 (or what ever choice rope you use over the branch), tie it to your eyelet on the pulley. Now, feed the loose end of the rope back into the pulleys eyelet. Make sure you have your antenna hoisting line fed over the wheel of the pulley and secured to something, make sure you have plenty of hoisting line. Start pulling the line that went through the pulleys eyelet. If you did it right, it will pull the pulley up along with your antenna hoisting line. Once the pulley is at your desired height, tie off that line, attach your antenna and hoist it up. If you ever decide to pull everything down, let out the rope holding the antenna, once its on the ground, grab both ends of the antenna rope and pull, the pulley and rope holding the pulley should work its way down. You wind up with two ropes needing to be anchored but its easy to remove/service/swap antennas.