The only comment I can think of is that the newer cars have more things that you cannot even diagnose, much less fix yourself. Therefore, the possibility exists that a W140 car will be more expensive to own.

As regards a Benz newer-looking and newer-feeling than your W123 car, anything from a W124 forward will qualify – I speak as an owner. As the 1987 300D Turbo is getting hard to find in decent condition (with a late head and all), I would suggest looking at a early-90s 300D 2.5 Turbo.

Another possibility would be a 1995 W124 with the OM606 NA engine. Our '96 W210 has the same engine; it is very nice although not as powerful as the later turbo versions. I don't think those engines ever made it into the S-class but I will defer to others more knowledgeable of the S-class.

I agree with H-guy that you should look at an S320 if you have to have a W140. The inline six gives you more power than the equivalent diesel, lots more than your OM617 but it will be easier to care for since it is smaller and has two fewer spark plugs (ugh!). BTW, Mercedes gassers are not terribly fuel-efficient, or so I have heard. You might want to get some numbers before you make a decision.

Jeremy

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"Buster" in the '95

Our all-Diesel family
1996 E300D (W210) . .338,000 miles Wife's car
2005 E320 CDI . . 113,000 miles My car
Santa Rosa population 176,762 (2022)
Total. . . . . . . . . . . . 627,762
"Oh lord won't you buy me a Mercedes Benz."
-- Janis Joplin, October 1, 1970