My wife owned a 2008 Roadster for 3 years, when the original warranty was a couple months away from expiring. We drove it to Texas to trade it in for a Fiat 500 Sport, and she's been much happier ever since.
In the 3 years she owned the car, there was over $20k worth of warranty repair work performed, including replacement of the BCM 3 times, and the flywheel twice (first one sent from Germany was damaged when it was installed, and the idiots at the dealer didn't test drive the car properly before returning the car to us), plus the clutch and pressure plate (pressure plate lost tension, and took out the clutch and flywheel at 9k miles).
The car will violently follow ruts in the road surface, so be warned.
If you want to drive the car in snow, the owners manual recommends that you purchase a second set of front wheels, and run the front tire size on all 4 corners. This is the best way to do it. Not too many snow tire choices in the rear tire size.
The exterior of the car looks great, but the interior is outdated, and cramped if you are tall and large. Especially the passenger seat. Not much room to lean the seatback back, because they hit the firewall (compared to a Porsche Boxster or Cayman).
The engine is peppy, but the manual transmission is clunky, and the metal shift knob will slip out of your hand at the worst possible times. First gear is really, really short.
Steering is vague, but will be fantastic if you never drive a better sports car, ever.
The car will go where you point it, and traction is limited by the electronic nannies, and your tire quality. No limited slip rear differential.
BC.