There are a few key words on your inquire, which are at the last of your post:

" ...and I want something that will hold its value and resell well in a few years."

Based on that I will definitely go with the CLK 500 instead of the AMG.

The basic problem is this: most AMG owners buy their cars to put them to the extreme constantly (who wouldn't???). That is the general idea on the used car market, hence second or third hand owners are really uneasy about buying AMG models. Proof of my statement: Both 2003 models are now the SAME price, while brand new the AMG was more expensive than the 500.

Although they are equal now, as time passes by, the AMG will depreciate faster and harder.

In terms of maintenance, I will be also a little bit less worried about the CLK 500. The AMG always has special parts which have to be constantly special ordered and are more expensive (I know this from a friend that owns an S 55 AMG, while most S 500 get their parts on site).

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A. Rosich
CL 500, 1998
S 500 L, 1998
E 320 T, 1995 [Sadly sold ]