Cylinder with irregular tree border

Dave’s solution is the easiest and most efficient, there are a couple ways to do it directly on sketchup though, the obvious one is show hidden geometry and with the pencil tool trace manually the contours, another easier way to do that is using Fredo’s plugin tools on surface that will make tracing the border a lot easier than with the native tools and the last option that comes to my mind is using also a fredo’s plugin that he released few time ago called pic 2 shape, it doesn’t work well with all the images, you can give it a try anyways. [Plugin] Pic2Shape - Extracting contours from images