Gearhead....you have tremendous tenacity.....(it wanes with age)
I have 70 acres on a mountaintop in Virginia.. As you, I wanted a perimeter trail....just wide enough for my Kubota. With a chain saw and limb shears I started and would get about 100 yards a day. I have a tractor width path along 3 sides now. (the last side has a pretty steep hill about 150 yards) A little uncomfortable for an old guy on a tractor. We'll see.
I've made several observations that I'll share. As you open up a trail the added sunlight causes the bordering trees to limb much faster. You'll have to drive thru regularily with a pruner. Also, the roots under the trail will sprout saplings faster than you can say "bush hog". You're going to need a tractor with a boxscraper and a bush hog.
And lastly.....you SCARED me when you pulled that tall pine over with the winch and then with all that pressure on it you cut it with a chainsaw. DON'T do that, release the winch pressure THEN cut it. That little girl is too pretty to lose her father. Nuff said, have fun, BE CAREFUL