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It may cost a lot, but the 2008 Porsche Cayenne GTS is a high performance on- and off-road vehicle. Current cabin tech isn't great, but a new version of the Porsche Communication Management system is coming out soon.
The 2008 Audi TT Coupe has an upscale look and is a blast on twisty roads. It might seem impractical and pricey, compared with other sports cars in the $50,000 range, but it is one of the best toys we can think of.