If you are not familiar with the 'heywhatsthat" tool - the coverage pattern is for a receive location six feet off the ground - roughly the location of a human eyeball. For specific locations, you put in the coords, click parameters and put in the height of the other end (AGL or ASL).
For your Matthews location, a path is indeed possible - although it has a bit of a problem - depending on the height at the other end(see attached).
The "pinch point" is actually covered by a lot of trees, so you have to clear those as well as the dirt there (second image attached).
Looking at the satellite map, I see quite a tall tower at the Matthews end, so I am guessing you are quite high on that tower and thus I would expect it to work.
I am too far north to reach down your way. "Assets" around here tend to be tall buildings where people are employed and various places where there are already VHF/UHF repeaters (hospitals, water tanks, hotels). I can suggest you look in a repeater directory.