Finally, I thought I would try again today. Downloaded the fingerprint from bike. Downloaded the new map from website. Put USB into bike, and for about an hour is just kept saying "authenticating." Pulled it out. put it back in. Walked away, came back, and looked like it had stopped doing anything. Just the radio was playing. So, I pulled the USB out and stuck it back in. Saw the famous "authenticating" and walked away. Came back a minute later and saw a screen asking me to make sure the ignition was in the ACC position. BINGO! I clicked YES, and about an hour and half later all was uploaded.
I looked at the NAV around my home, however, and it doesn't even show a new Freeway that runs near my home. I guess it wasn't completed until after Qtr 2 of 2014. Oh well, I'm as updated as I can be now. Harley really needs to make this easier.