Date registered: Feb 2008
Vehicle: 2004 W220 (S430) ; 2001 R129 (SL500) Sport
Location: Alabama Gulf Coast--formerly Charlottesville, VA
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No direct experience, but I can tell you a couple things that might help.
The CLK55 is the high-performance AMG tuner version of the car. It has (I believe) a supercharged V-8 engine that generates close to 500 horsepower. It also has larger brakes and a sport-tuned suspension (read: it rides firmer). It is a rocket ship that will get you in a lot of trouble in a real hurry if you aren't used to that kind of power. Compared to the CLK550 it will also be less economical and will cost a ton more to insure. Repairs will be more (maybe a LOT more) expensive than the plenty expensive repairs on the 550. Tires will be as much as $150 a corner more expensive since it takes W-rated tires, plus they wear much more quickly than lower speed rated tires.
The CLK55 was a very expensive car new, but they depreciate quickly because of the expense of owning them.
The CLK550 has nearly 400 horsepower, so it is no slug. I have the 7-speed transmission in my W220 and I'm averaging 22 mpg in mixed driving. I get 28 at a steady 80 mph. My engine is considerably less powerful, but my car is a bit heavier, so you might not get the same mileage, but it should be fairly close. It will still be relatively expensive to insure if you are young or have a blemished driving record.
Unless your wife is a hot-rod, she will never use the horsepower in the CLK550, and she won't notice the missing 100 hp that comes with the CLK55. I'd buy the AMG, but it would be for me. As I read what I just said, I'm not so sure I would; the CLK550 has plenty of grunt and handles reasonably well. You won't use the potential of the AMG tuning, brakes and engine one time out of a hundred.
I'm a little surprised the CLK550 is more, even though it's newer--the AMG version was probably $15k more when new.
The repair and maintenance costs would be the deal breaker for the AMG for me. Some of the repair parts costs for that drivetrain will stop your heart.
Good luck on your decision--you have an embarassment of riches.
"Don't pick a fight with an old man. If he is too old to fight, he'll just kill you."--John Steinbeck