In my opinion, any diesel that is still running is a good model and year. To give an honest, well educated answer, I will have to drive a car from each year, of each model.

I know a family, where they only buy 1983 model year diesels. They have several SD's and 300D's from that year.

Believe it or not, many a mechanic will contend that for some reason or another, 1983 was a "good year."

Just to help really confuse the issue, I wouldn't be so quick to write off the California '85s. I've had mine for 11 years and 100,000 miles without any problem. Would I prefer not to have a trap? Of course. But MBZ paid for all the extra maintenance and it's given me zero problems so as far as I'm concerned it's virtually no difference. I'd vote for the '85 if only for the tranny improvements.

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LRG
1987 300D Turbo 175K
2006 Toyota Prius, efficent but no soul
1985 300 TDT(130K miles of trouble free motoring)now sold

The 85s (and the 87s for that matter) are great cars, but any car that currently or previously had the trap on the existing motor, I will bet, is statistically more likely to have major engine work down the road.

My brothers 85 california 300TD got a new engine at 120K miles because of a catastrophic trap failure. His crate engine warranty just ran out, so that should give you some idea of how long ago it was replaced.

My 87 sdl has a new head, probably because of overheating related to a lame PO and/or the trap.

Maybe I am biased, but I woundn't buy a car that had a trap oxidizer unless I was really comfortable that the engine was rock solid.

So for me that means any 84, maybe any 83 and the federal 85s.

later

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84 300TD - 235k - Farbe "Surfblau" bought at 213k
87 300SDL - 131k - Farbe "PimpGold" bought at 115k
00 Klepper Faltboot Expedition Double

A 240D and a 300CD.

One big advantage to sticking with one year is that you can assemble a body of knowledge, parts, arcana, etc., specific to that year, which you can then apply across your fleet.

Same for my '73 VW convertible (had since new), and my '40 and '49 Packards.

Someone I know in Texas has been collecting 1940 Packards exclusively for about 25 years. He published a book last year on this particular vintage (Packard held for 50 years the US market niche Mercedes later took over).

my 1952 Shakespear Sportcast level wind casting reel is the best year for Sportcast reels bar none............
William Rogers......

keep it simple, overbuilt of the best materials, reliable, affordable, well conceived by engineers and not built to a price point, with styling that holds its own very well against later and present models.

I love VW beetles (the real ones) for the same reason...they're the opposite end of the continuum from the 240Ds. Model A Fords and "Model L" Lincolns of the '20s were other examples of the same design and durability philosophy as applied to two different market niches.

Regarding the KISS theory, I agree with Larry. The simplest diesel I've ever owned was my '77 240D 4spd. Was easy to work on. parts were readily available, not very difficult to troubleshoot issues.. I enjoyed the 4spd because I would crank the stick out of the engine/rev it up to make it move. Especially merging into the highway. Also, very, very solid vehicle. Had very few headaches with this car. I can say I really got my monies worth out of this one.

But the most comfortable, safe, and solid diesel would definitely be my w126/300SDL.
Just had to add it somehow...

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99 C230K Sport
87 300SDL
81 300SD

I'll have to agree with that.