As far as the road hoping, I am afraid that you are just like the rest of us and stuck with the POS crappy Nanny Nav that sucks and can be beat by a $100 Garmin. So much for a $4000 POS option.
Now the calendar I am not sure about. I don't think I ever used it. I guess I would have if it would sync to an Iphone but Apple has to be unique.
The 10.1 software is available:
Navigation DVD Generation 5 v10.1 but it will not help you much with the accuracy of the GPS and it poor route selection capability.
Also, as far as your clock problem on your other thread, just to prove what a peice of crap the Nanny Nav is, it does NOT get the clock automatically from the GPS sat signal like any $100 Garmin does. Instead you have to manually set the clock in two places. First, you have to set the clock on the Multi Function display using the button on the steering wheel. Once that is done you also have to set Daylight savings time either on or off in the setup of the Nav itself. Otherwise, your arrival times will be an hour off. Like I said, truely a POS.