After many many attempts and reading multiple posts about this same issue I have still not solved it. After installation of Ubuntu Server via USB I am met with "Reboot and Select proper Boot device or Insert Boot Media in selected Boot device and press a key". Ubuntu Server boots when the USB is plugged in. Although it boots into a black screen and I am forced to use the tty1 console. (unrelated?)
The HDD is a 3TB so I am not entirely sure that could pose a issue with the installation. Ubuntu Server is installed on the 3TB HDD at /dev/sda. I have installed GRUB manually to /dev/sda. I have ran the Boot Repair tool via Live CD using the "Recommended" default option. I have manually partitioned the drive as well.
As of right now I am setting up SSH so any log requests can be fulfilled.