Yes, was firewall issue. Fooled me since some of the communication worked and the AV/Firewall was configured to allow the imaging program to pass through. But it all worked when the firewall was turned off. This took a bit of work as it is a school district computer and resists such efforts.
Thank you! I was able to download NI CompactRIO which includes NI MAX, opened it up, was having issues getting it to see the roborio for a second. I restarted the robot and plugged the USB cable into a different port on my computer, not sure what made it happy, but it found it, then I updated the firmware to v6, which was already on there. After using NI MAX, I was able to go back and reformat/reimage the roborio using the FRC roborio reimage tool! Note: I am not sure of what packages are absolutely necessary when installing NI CompactRIO, but it did take some time to install because I did install everything, maybe 20 minutes, idk. I also had my firewall off as suggested.