Unable to flash: Error: probing the target board failed. and boot: Error in NvTbootLoadBinary: 0x14

The above is up to the VM manufacturer. The Jetson software has no control over how USB might fail on the host PC. People tend to think a VM is an actual computer, but it isn’t…it is a computer emulation, and if the emulation is flawed, then there is nothing the Jetson software can do about it. This is in fact one of the points of a VM: One could run unsafe software in it and the software would have no ability to change anything outside of the VM. This is the very definition of “the Jetson has no control over it”.