Been flying model helicopters for quite sometime, I started back when we had to scratch build our own which required a lot of machine work. Which by the way is how I learned how I learned to use a mill and lathe.
I was also a factory sponsored pilot for a few years doing demos and such at air shows. I don't know if you were joking but even for someone as experienced as I trying to fly a line over the top of a tall tree would not only be extremely difficult it would be very dangerous. can you imagine what would happened if that line snagged. On the other hand I used to practice inverted flight by using a model helicopter to blow leaves on my driveway and lawn.
Anyhow I have tried many ways of getting lines over tall trees and nothing seems to work as easily and safely as a pneumatic tennis ball launcher. I've built quite a few of them, unfortunately some ham always comes along and offers me a ridiculous sum of money for them so I always end up selling them and never seem to have one on had when I need it.
Of all the methods I have used the sling shot seems to be the most dangerous. It's been my experience that its really only useful on very calm days. If you try and launch a line on a windy day more often then not the light weight fishing line tangles on the sling shot arms which usually results in the weight either not traveling far or rebounding back at the shooters face. More often then not it misses the shooter but that one time it hits you is enough to sour you on using them. At the vary least I highly recommend wearing safety goggles.
Anyhow the whole point of this post is to strongly recommend wearing safety goggles when using a sling shot to launch lines. This advice went unheeded by an arrogant ham last field day. The unfortunate result was a trip to the emergency room with a serious eye injury. So if you plan on using a sling shot please wear safety goggles.