The driver configuration looks good. The most likely reason that it isn't is that the"Metadata management" option on the "Sending books to devices" page of the preferences is not set to automatic.
Or, if you have the KoboTouchExtended driver installed, you could be configuring the wrong driver. Check the driver when the device is connected. Right-click the devices button and select the driver configuration option thee. This will show the configuration for the driver being used.
The "Update cached metadata to device" is for calibre's use. It updates a file in the root directory of the device to help calibre match the books on the device to the library. The device does not use it.
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