Update: So I found the fix for both issues. The one is simple.
If you are prompted to allow access to the file system but nothing comes up you need to go into device manager and totally uninstall and delete the oculus ADB driver.
If you aren't prompted at all the only fix I found was to Factory Reset the Oculus Go from the Oculus App and add it back. Upon doing that it worked when connecting to my PCs.
I saw that the Oculus Go can be connected to a PC for file transfer however every PC I connect it to no prompts come up and I never see the drive in my file system.
DK1 Order No: 574XX (US)
DK2 Order No: GP-1055XXX
CV1 Order No:6130000XXXXXXX