I'd look for a 2000-02 E320. All the problems were worked out by that point, and you get all the nice updates.

I have owned MB's for a long time, and know many people who own both new and old ones. The $2k-$3k a year for maintenance and repairs rule is pretty good. Sometimes you come out ahead, sometimes not. Of course you can drive them into the ground for much less, I have done that too. Of course if its new and under warranty its much less, usualy only like $500 a year for the services.

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2006 CL500
2009 C300 4matic
1969 280SE
2023 Ram 1500
2007 Tiara 3200