Ahh the W140 bug has bitten you, it truely is one of the finest sedans ever made by anyone. Mercedes spend $1 billion dollars designing them back in the late 80's, I don't think anyone can afford to make such a car again. They delight through share attention to detial. Driving one will be deadly, your 300D will feel like a John Deere in comparision, the Honda isn't even in the same ball park. Nothing eats highway miles like a properly sorted modern S class. You must keep a carefull eye on your speed as the car will want to waft into triple digit speeds with ease. In a W140 the only way you know your doing 120 insted of 70 is because the scenery is moving faster.

The model you should look to buy is a late production(1997-99) S320. They are "simpler" since they were the base cars, and the M104 gives you all kinds of room under the hood. While not as fast as the larger motors, the M104 with the splended 722.6 gearbox move the car along nicely. It won't have the same punch at passing speeds as the big motors. If you want punch the 5L V8 is the way to go, unless you want the V12 of course. Both are similer speed wise, but above 100 the V12 will pull away. Top end should be about 175ish.

I would not buy this W140 for a couple of reasons. One it has to many miles, you want at least half that. Two its an early production car so it will probably have all those cool early production issues, like a failing wiring harness. Three its the small V8, if you want to spring for the V8 go for the S500.

IMHO the best W140 is the S600 flavor. Every time I ride in my friends perfect 1995 I am amazed at how good it is. That V12 just has a never ending surge of power and would be more than happy to pull the car along at 150+ until the tank ran dry.

Surprisingly it has been more reliable than my SDL, but has covered far fewer miles. However keep in mind your buying a top of the line car, so when they do break its never cheap. Spending more on the best example you can find should help minimize this.

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2016 Corvette Stingray 2LT
1969 280SE
2023 Ram 1500
2007 Tiara 3200