I didn't mention this in the original post but I can communicate with my family who are on 935's 5 miles away on channel 17, so I don't believe it's an audio mike issue.
From what I can gather while reading, it appears to be fairly common to be able to receive farther out than you can transmit, particularly when in terrain like I am with trees, elevation, and buildings in the line of sight.
I'm fairly disappointed they steered my towards the coax they did knowing I was going to be running UHF. I imagine I have a lot of loss with 75 feet. Spent a lot of money on it as well, so I don't want to just swap it out.