Interesting insight from a Mercedes techincian...

If I had 20k to throw on a used car with 4 doors and a 3 pointed star. I'd be looking for a 2000+ E430. You should be able to purchase a low miles ~50k or so 2000 or 2001 E430 for right around 20 - 22k.

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Daily Driver: 02 E430 4MATIC
In the family: '03 E500 // '04 ML500 // 64 220SE