Firstly, the "?" is not an issue. That is a generic icon because calibre doesn't have one for kepubs.
The problem seems to be the files are not being renamed. I can see:
Code:
DEBUG: 83.4 KoboTouch:upload_cover - path='H:\Huber, Anna Lee' filename='Treacherous Is the Night - Anna Lee Huber'
DEBUG: 83.4 filepath='H:\Huber, Anna Lee\Treacherous Is the Night - Anna Lee Huber.kepub'
That last line should have ".epub" on the end. The driver is supposed to rename this when the kepub is sent. It appears to be because you have the KoboTouchExtended driver enable but have the "Enable Extended Kobo Features" option unchecked. That is a bug, the rename should always be done when a kepub in the library is sent to the device. But, I'm not that surprised that it is hasn't been noticed as the extended driver is fairly pointless if you don't have that option enabled.
My usual recommendation is to either use the extended drive with the "Enable Extended Kobo Features" option on so that books are converted automatically. Or, stick with the built-in KoboTouch driver and convert to kepub if you only want some books sent as kepubs. From the configuration, I assume you are sending epubs for yourself and converted kepubs for your wife. In that case, stick with the KoboTouch driver.