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Overall, lately it seems that the newer models are less bulletproof than the ones in the early nineties (more or less) according to the quality surveys that
monitor this kind of thing. That's because they were built more to a price point than to the company's original credo "The Best or Nothing" Look at the ads you see for them, saying how cheap you can buy or lease one for.
That's not to say you can't find a great example. Lots of folks own the newer ones and are very happy with them. But there are lots ot "Toads" out there now also.
Certainly, with the introduction of the W140 for 1992, complexity skyrocketed and quality went down somewhat.
For sure after 1996 you would need access to an OBD II diagnosis analyzer at the least. Fixing electronic gremlins in these new ones won't be for the faint of heart either. Things in that area have gotten so complex that some Independent mechanics would rather not have to try and fix them
This isn't really an answere to your question, but were I to get another Mercedes, a newer one, I would definately try and get one with a Starmark Warranty. True, they are not cheap, but they are like insurance and could
really save you if something big and difficult went wrong.
The passive/active safety features are still good and getting better so a good argument for them is still, you can survive and walk away from a bad accident, that would be very quite horrible for you otherwise.
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 1991 560 SEC AMG, 199k <---- 300 hp 10:1 ECE euro HV ...
1995 E 420, 170k "The Red Plum" (sold)
2015 BMW 535i xdrive awd Stage 1 DINAN, 6k, <----364 hp
1967 Mercury Cougar, 49k
2013 Jaguar XF, 20k <----340 hp Supercharged, All Wheel Drive  (sold)
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