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Most fun car: 1966 Shelby GT350, (yes, it was a real Shelby). Taught my ex-wife and daughter how to drive 4-speed manual transmission in that car and we didn't burn out the clutch. But, we did inflict significant wear on the rear tires.
Most practical: 1998 Chevy Tahoe, 2 door, 5.7 liter V8. Still own it at 176k miles. Lowest maintenance cost and most reliable vehicle I've ever owned and I've owned German, English, Japanese and American vehicles. Yes, fuel is US$4 per gallon here. I live in Texas so a truck is required in the garage.
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