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I have had a great time with my E500, but do live in fear of something breaking.
I believe the E55s have an airmatic suspension, as does mine, which can be problematic. The electronic brakes are known as well, but MB warrantied them for 10 years because of it. I have yet to have an issue with either of them.
The only issue I've seen first hand with that motor is the supercharger getting hot and kicking itself off in a friend's CL55. Then the car becomes a dog. Anything AMG specific, such as the brakes and motor components, is going to hurt.
Is there any reason he's wanting to go E55 over E63? Supposedly they are much better motors, and the electronic brakes were eliminated. Quality ratings for MB went up quite a bit starting around then as well, and the styling upgrades were fantastic. Both would kill just about anything at a stoplight, though.
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