Thank you for all of the suggestions!
It turns out it was actually a very simple problem. We were trying to deploy our code via Ethernet cable through the D-LINK, when we should of been using an USB A to USB B cable to deploy code directly to the roboRIO! This is why it appeared that the roboRIO had to be re-imaged each time, when it reality all we had to do was connect the cord. Again, thank you for the all the help!