Hi,
the reason why we do not support flashing using a VM is that the device will be connected and disconnected multiple times throughout the process of flashing, which may not be handled correctly by a VM, and it’s very likely in your case.
I think you may dual-boot your Windows PC to get an Ubuntu system, or see if Live USB works:
Trying to install JetPack using live ubuntu - Jetson & Embedded Systems / Jetson TK1 - NVIDIA Developer Forums