From past experience just getting the land where you can see it helps a lot. We have found out not turning over any more soil than needed keeps the erosion to a minnimum. The first thing I would do is get rid of some/most of the scraggly small diameter trees. We used a setup like the "right of way" folks use (An old surplused 1960's GA DOT cutter). Clear a few spots to pile bigger diameter trees and run over the rest with the huge cutter. Anything left big enough, put into pile. What is eventually left is short stubs that can be cut down a little further if the ground is not to rough or rocky. Not turning up the dirt made for a lot less mud. We have a lot of land from Atlanta north to TN and NC that looks like your non winter shots from all the tornados some of which were spawned from the hurricanes in the past 10 years, and some that look that way after the pulpwood harvesters leave. You stand back and look and don't know where to start. Back to tractors, most of the right of way tractors are New Holland's, don't know why . Cobb County Tractor north of Atlanta was setting up a few 2 weeks ago, by removing rear fenders/ROPS/tires/wheels and replacing with a heavy duty cage. Rear tires were re-capped aircraft tires and about 6' tall and 3'+ wide on a small diameter rim. The wide tires made them look very stable. The mowers looked like they could cut down light poles. The friends I mentioned above have property that backs up to an underground gas line on the east and high voltage power lines to the south and we have followed up on a few sections behind the RoW folks with my and my friends tractors with 5' and 6' brush hogs and the property looks about like Your neighbors property You pictured, although the grass is not high quality, mostly weeds/field grass. Good luck and get started while the weather is cool and no yellow jackets/wasps.