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Most people on the internet talk about Benz problems. From my own, friend, and family ownership, including some years and models that are allegedly troublesome...the vehicles are really well built.
If you ask me I would get the E500. The 113 V8 engine is INCREDIBLE...you wouldn't believe the pull of the 500 engine. The 722.6 automatic is about as tough as they come...same one used in super heavy duty Mercedes like the AMG's, Sprinters, and V8 or V12 forced induction cars.
Problems will be that the suspension is super nice and smooth and with that comes maintenance. The air suspension may need parts BUT you can get Goodyear or Continental airbags for around $400 or so instead of $3000 from Benz. Further, the earlier years of that E series had electronic brakes, which are weird and require equipment to work on but that is to be accepted.
If you want simpler get the C-class but it won't pull or sound ANYTHING like the M113 V8 in the E500.
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