Alright, from some more driving I noticed a number of interesting “quirks and features (Doug Demuro style)” with the drive on nav system.
1) As I first discovered in the video, you have to press the “drive on NAV” button on the navigation screen to activate it even after having activated the feature in the settings screen. However, oddly enough, this can only be done on a street, whether that be a surface street or expressway or highway. This means that if you enter your destination while parked on a driveway or in a parking lot you have to wait until you drive onto the street until you can activate the feature for the given route. This is unnecessary and requires you to tap a button on the screen while driving, which makes no sense. It is more safe to do it before driving rather than while driving but the system doesn’t let you do that.
