Getting around the upload problem with CH340 usb-serial i found installing the 2019 driver works. Newest driver does give the "A fatal esptool.py error occurred: Cannot configure port, something went wrong" error.
Strangely with newer driver the serial console works fine, just the upload does not.
And it works until windows10 restarts. Then it "updates" the working driver with the not working one. To prevent this, make the old 2019 driver in sytem32/drivers read-only, not deletable. Name is CH341, 3 files.
I would recommend instead using the intended "roll back" mechanism for pinning a driver version. When you do that, Windows understands that you are intentionally using the older driver version, and won't revert the change by updating it once again. In case it will be useful to you, I'll provide instructions:
Select View > Devices by type from the Device Manager menus.
Open the "View" menu.
If there is a ✓ to the left of the "Show hidden devices" menu item, click on "Show hidden devices" to disable it.
Open the "Ports (COM & LPT)" section of the Device Manager tree.
You should see a port identified as "USB-SERIAL CH340 (COMn)" under the "Ports (COM & LPT)" section (where "COMn" is some serial port e.g., COM4). Double click on that item.
The "USB-SERIAL CH340 (COMn) Properties" dialog will open.
Select the "Driver" tab of the "USB-SERIAL CH340 (COMn) Properties" dialog.
You will see a "Roll Back Driver" button in the dialog. If it is not clickable, perform the following instructions:
Click the "Update driver" button.
An "Update Drivers Device - USB-SERIAL CH340 (COMn)" dialog will open.
Click on "Search automatically for drivers" in the "Update Drivers Device - USB-SERIAL CH340 (COMn)" dialog.
You should now see the driver installation wizard update the driver. Wait for the update to finish, as indicated by the message "Windows has successfully updated your drivers" in the dialog. It is possible you will instead see the message "The best drivers are already installed". If so, please stop following the instructions here and reply on this forum topic to let us know. I'll provide alternative instructions you can follow.
Click the "Close" button in the "Update Drivers Device - USB-SERIAL CH340 (COMn)" dialog.
The dialog will close.
Click the "Roll Back Driver" button in the "USB-SERIAL CH340 (COMn) Properties" dialog.
The "Driver Package rollback" dialog will open.
Click the radio button next to "My apps don't work with this driver" in the "Driver Package rollback" dialog .
Click the "Yes" button.
The "Driver Package rollback" dialog will close.
Click the "Close" button in the "USB-SERIAL CH340 (COMn) Properties" dialog.
It does indeed matter. The legitimate WCH CH340 chips work perfectly well with the modern driver version. It is only the sketchy blank chips found on the supiciously cheap Chinese boards sold by unscrupulous sellers on the less vigilant marketplaces (e.g., AliExpress) that misbehave when used with any driver version newer than 3.7.2022.01.