FOR CVO's With Keyless / Keyfob Ignition. Whole different process!
Finally figured out why this was not working after tons of attempts. It turns out there is a completely different method to use when you have a keyless ignition with a key fob.
DO NOT manually turn the large center ignition knob to the right as is described in the numerous "You Tube" videos on this topic.
DO NOT turn on the power switch on the brake side handle controls.
.... All you have to do is set the bike to accessory mode by pressing the large flat mode selector button on the top of the clutch side hand controls. The radio will boot up. Make sure the radio is turned on.
NOW plug in your USB drive with the ISO file into your usb port.
There will be a button on the touch screen saying something like "No Playable Media Found" Hit that button.
Next, a screen will appear saying "INSTALL SOFTWARE" with a "YES" and "NO" button at the bottom of the screen. Hit "Yes".
DO NOTHING AT THIS POINT. The software will start to install now. The head unit will automatically powerdown and power back up again.
DONE!
This drove me crazy for a long time....