I had similar problems with an XIAO ESP32C3 and the nRF52840. My windows 10 laptop and Arduino would work for several compiles, then just stop with the XIAO boards. My Arduino board worked flawlessly every time. After trying to figure out when to double tap which reset button, then quickly select the correct USB port again… I finally gave up and went over to circuit python. Lots of people have the USB drive issue and I did not find a solid solution that permanently fixed it. I’m sure there is a solution, I just don’t have the patience to find it. I was not very far along in my project so switching over was not an issue for me.