We bought a clean one owner '95 C280 with 100K miles on it and 6,000 miles later LOVE the car. For less than we'd pay for a used Honda Civic we're driving a Mercedes! A lot of people lease these so they can impress parking valets and there are lots of good used Mercedes to choose from. We put $2k into it for the 90k service as well as new shocks but it's been well worth it. It's super on the highway and we love the smooth power of the engine and the awesome stereo. Classic styling means no one knows we paid $7k. Higher than TMV here but that's S.F.
The most amazing thing about the car is its turning radius, which comes in handy in San Francisco. Making a quick U-Turn to grab a parking spot has never been easier. In general everything is very well thought out. There really is a difference with these cars.
Mileage is poor (16mpg City and 24 for long trips) and premium is pricey