They say the best ones are the newer ones. Like a 99-2000 model C280. Personally My 2000 C280 has been trouble many many times. Its very reliable and always starts and runs but it very very high maintance. Its been in the shop more times in 2 years of ownership then my E320 AND 420SEL combined.

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2015 ML350 4Matic. Wifes DD
2015 GLK350 4Matic. My winter DD
2012 E350 4Matic. Road Trip car
2009 CLK350 Coupe Designo.Kleemann Tune For nice days/DD
2006 CL600. V12.Eurocharged Tune. Enough said
2005 CLK55 AMG Coupe.Kleemann Tune. For the sound and style
2004 CLK320 Cabriolet. 2005+ Interior swap. For the sunny Florida days & beach days