Thats interesting they use USB and Activation card to update map data. I was at an Australian dealer and they apparently use a DVD which seems a bit archaic. This is for a 2014 Prius V!
FWIW, the local Prius parts department said the navigation update for our 2014 Prius is # 86271-HDD07-15, $169, and will require THEM to do the installation. Maybe the "HDD" implies Hard Disc Drive?
Bargain with them. I got 10% off the part by grumbling and service cut the time to install in half. Make it clear they can accept some money or get none is the line to take. I wasn't abusive, just they didn't want someone bad mouthing Toyota's policies or their sales people in the service department. (I had been told when I was buying the car updates were over my phone implying that they would be Garmin/TomTom like).
So is now or a couple months later the best time of the year to update? I seem to recall someone mentioning spring but I'm not sure. I have a 2012 Plug-in that has never had the map updated.
Talk to your dealer and see what the date of his latest update is. Get both the firmware update and the maps and don't pay list. It is somewhat negotiable. The November update should be available.