I don't see why you're not going up and down the hill. going side ways is dangerous. you can drive up to the top of your property, and set the ratchet rake down, back drag it. as for the bottom drive forward and stop at the edge of woody cliff. going side ways the tractor is going to have a tendency to slide down hill, especially on grass.
I have a ratchet rake. it work awesome. I've taken down small trees. about and inch to inch and a half. roots and all. its pulled out rocks. I think you just have to get familar with it maybe on a level section then tackle the hill side.
best of luck