I own a 2001 CLK 200 Kompressor cabriolet, purchased almost a year ago with slightly over a 100.000km on the odometer and only 2 owners. The car had a few things that neded to be sorted out, especially the handling that was kind of vague. A full set of shock absorbers and a steering damper cleared most of it. Other than that there were slight cosmetic issues inside that got easily fixed. I had to change the water pump and a couple of hoses that were leaky. Most annoying was a problem with the gearbox that needed a rather costly visit to a specialist. And the last thing to give me trouble was the rear window regulator that had to be replaced.
Otherwise it is a really nice car that I enjoy driving every day.
I own another CLK in my home country, France, a 1999 320, also a convertable. Perfect for holiday rides in the countryside. In 5 years I only had to change the baterry and a sensor for the aircon.
Other than that, I have been living in Singapore for the past 20 years, maried and a 15 year old son.