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