Outdoor Home Automation

I thought I'd start a thread about home automation. I was trying to do something which I though would be simple but it's not... I have some insteon switches in the house, and was looking to move a bit outside.
What I'd like is for my system to detect when a car pulls into the driveway (motion detector at the end of the driveway). When the car pulls into the driveway, the house front lights, and the front foyer lights to turn on. The front lights would be on a timer so they turn after ten minutes. When I'm leaving the house, I press the 'Going Out' button, which turns off all the lights in the house, turns down the thermostat, but turns on the front house lights on (again, on a ten minute timer). If the car drives out of the driveway in that ten minutes, it does not reset the timer, etc because it knows I'm leaving... Of course, no lights would turn on if it's light outside, and there would be an override switch that allows me to manually turn the lights on or off (for when I'm shoveling the driveway, etc).
First I'm wondering if anyone has tried something similar and if so, how they accomplished it and what their success is/was. What technologies they used etc. (I don't mind moving to a different technology here, as none of the components save the 'going out' button would interact with the inside lights)
Next, I don't think I can do the above without running a computer 24/7, which I'd like to avoid but, if I did do that, I was wondering if people could recommend some software, etc
Lastly, I'm wondering about motion detectors -- does anyone know of any good detectors that could survive a Canadian winter? I don't want to buy something that bums out once it drops below -20.
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