What are some of the problem areas I should look at?
I own a 1984 Mercedes 190E and never had real problems with this 23 (!) year old car. Also, up to several weeks ago I had a 1985 Mercedes 300TD, which was the most reliable car ever! Unfortunately, this one has been totaled in an accident and I had to buy another car. My Mercedes mechanic, whom I know for 20 years and really trust, told me to go with an E-class (not an S-class) because an E-class is more reliable and the costs of regular maintenance is lower.
The mechanic recommended an E320, but no older than 2000 because 1999 and older had transmission problems (I do not know if this is the case with an S-class as well.)
I bought a 2000 E320 with 60,000 miles on it and I'm VERY happy with it.
Of course, as with any used car, take it to a trusted mechanic before you buy. If a seller doesn't want you to take a car to YOUR mechanic, you do not want this car.
Hope this helps.
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