My lawn is just shy of 4 acres and is tree-lined on 3 sides. It also has several large trees scattered across it. Three 50-75' high silver maples, three decorative cherries, a black cherry, two walnut and one chestnut trees, a couple of willow trees.
If I had to rake, I wouldn't stand a chance. I chop up all of it that I can drive across with the lawn tractor.