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Like someone else mentioned, the Rogers stick isn't going to get you any GPS functionality. I'm not sure if the iPhone can pass NMEA data via BT or something similar but you'd minimally need that to use it with any mapping software.
As for software recommendations, try:
Microsoft Streets and Trips
Microsoft Map Point
Garmin MobilePC
iGuidance
Right now, I am playing around with Garmin MobilePC. It has a interface that's very similar to the Garmin portable GPS units. You can use it with 3rd party GPS units as well as Garmin handheld units. (I have it paired with my iBlue Photomate BT GPS datalogger on my netbook)
I used Map Point many years ago, but it doesn't have the voice navigation so it's not exactly ideal for driving. (I used it back before portable units were mainstream) iGuidance used to be the defacto laptop standard software (I've never used it) so it may be worth trying.
Like someone already mentioned, your best bet is probably a portable GPS unit. It's small and it's less likely to be a distraction. It also beats hauling around a laptop when you want to just go find the nearest mall to pick up some groceries and then having to find somewhere to hide the laptop (or worse have to carry it with you)
Tethering is alright if you have a plan that supports it. Just remember that 3G coverage isn't everywhere, and you may end up with a super slow EDGE connection in more rural areas (or no connection at all in some places)
Also, if you haven't already, pick yourself up an inverter so you can power your laptop. It would suck if you're using it for navigation and the battery dies on you. Also, make sure your car battery is in good shape. My last car battery (which was on it's way to a slow painful death) was a little low on voltage and the inverter would complain (by beeping incessantly) when the voltage dropped too low (usually when I was idling). It was annoying as hell, but the load may cause the battery to also die prematurely if you have a lot of devices hooked up to it.
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