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As a tech car, the 2010 Subaru Outback is average at best, lacking many modern amenities. All-wheel-drive is its saving grace, giving it good weather capabilities.
As a tech car, the 2009 Subaru Impreza GT rates very poorly, offering few modern conveniences, but the all-wheel-drive system will give peace of mind in slippery weather.
The 2008 Subaru Tribeca is enjoyable to drive, and incorporates a few good tech features. However, it also has some real flaws, which could affect your long-term satisfaction with the car.