Allmost exactly the same issue.
Board: Wrover v4.1
Vmicro: 2020.618.1
Zadig WINUSB driver installed.

I deleded c:\ProgramData\VMicro\tools\ folder in hope it'll be reinstalled. And it was so.
Below output I got:

Program MAX86150_M5 size: 1 123 203 bytes (used 86% of a 1 310 720 byte maximum) (167.21 secs)
Minimum Memory Usage: 40128 bytes (12% of a 327680 byte maximum)

# Copy build result to 'Project>Property Pages>Intermediate Directory'
# Destination: file:///D:/Arduino/Proj/ESP32/Wrover/M5Wrover/MAX86150_M5/Debug/

Uploading 'MAX86150_M5' to 'ESP32 Wrover Module' using 'F2232H Dual RS232'
Uploader started for board ESP32 Wrover Module
Uploader will use programmer name: espf2232h


Downloading tool to 32-10.0.1.zip
Installing tool. License: OpenOCD - (GNU GENERAL PUBLIC LICENSE)
C:\ProgramData\vmicro\tools\openocd-espressif-esp32-10.0.1\bin\openocd.exe -d2 -s s/" -f "interface/ftdi/minimodule-lowcost.cfg" -f "board/esp32-wrover.cfg" -c "echo -n {****[vMicro]**** Uploading App :}" -c "telnet_port disabled; program s/partitions/boot_app0.bin} 0xe000" -c "echo -n {****[vMicro]**** Uploading Bootloader :}" -c "program s/sdk/bin/bootloader_dio_80m.bin} 0x1000" -c "echo -n {****[vMicro]**** Uploading Sketch :}" -c "program MAX86150_M5.ino.bin} 0x10000" -c "echo -n {****[vMicro]**** Uploading Partitions :}" -c "program MAX86150_M5.ino.partitions.bin} 0x8000 reset; shutdown"
Open On-Chip Debugger  v0.10.0-esp32-20190313 (2019-03-13-09:57)
Licensed under GNU GPL v2
For bug reports, read
	http://openocd.org/doc/doxygen/bugs.html
debug_level: 2
adapter speed: 20000 kHz
Info : Configured 2 cores
esp32 interrupt mask on
****[vMicro]**** Uploading App :Error: libusb_open() failed with LIBUSB_ERROR_NOT_SUPPORTED
Error: no device found
Error during upload using programmer
The uploader process failed

Error: unable to open ftdi device with vid 0403, pid 6010, description 'Dual RS232-HS', serial '*' at bus location '*'
The uploader process failed
The uploader returned an error
# Copy build result to 'Project>Property Pages>Intermediate Directory'
# Destination: file:///D:/Arduino/Proj/ESP32/Wrover/M5Wrover/MAX86150_M5/Debug/

** OpenOCD init failed **
shutdown command invoked
Warn : Flash driver of esp32.flash does not support free_driver_priv()
Warn : Flash driver of irom does not support free_driver_priv()
Warn : Flash driver of drom does not support free_driver_priv()
 

What i did wrong?

Thanks in advance,
Vladimir

Sorry, forget about it.
UPD:
I launch the ptoject with VisualGDB and firstly got the same error. But when I launch Debug Test on target with reset button pushed, it passed the test. Unfortunatelly it is the only success, because I got excepions: 
Received a SIGTRAP: Trace/breakpoint trap
Received a 0: Signal 0
during debug.

Thanks for answer, Simon.
As I mentioned above, proper driver installed and VisualGDB recognized debugger.
IMHO, something wrong with VM openocd.

Thanks for the information.

We cannot compare directly to Visual GDB as we are likely using different builds of OpenOCD, which may differ in the driver required (The OpenOCD in Visual Micro is the one supplied from Espressif)

Was the driver shown here installed via the Zadig tool?  I only ask as it doesn't state the version in the Zadig window, which it should to confirm it is the same 6.x version of the WinUSB Driver. This can also be confirmed in Device Manager as an alternative (if Zadig doesn't show it for any reason).

The Log shows a successful upload via vMicro + OpenOCD so the debugging should all work now. 

Could you try uploading, press reset on board, attaching the debugger, and send the log file from the build folder as detailed here?

Thanks for the logs and information.

The ESP32-DEVKIT shows a succesful upload via JTAG, so all Drivers are in place correctly, and OpenOCD is working.

Could you try:-
1) Set Build Configuration in VS to Debug
2) Set all ESP32 + Devkit Debugging options as needed
3) Connect to Debugger and Upload Code
4) Press reset on board
5) Debug > Attach To Process
6) Attach the log file from the build folder as detailed here?

This will show more information about the debugging starting from OpenOCD.