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If it were me....
... I'd waive the requirement for a stick shift MB.
Don't get me wrong, I enjoy a manual transmission.
I currently have 4 in the fleet: 54 Chevy 1/2 ton stepside with 3 on the tree, 68 MGB with 4 speed with OD on 3 and 4, 89 Dodge-Cummins with getrag 5 speed, and a 99 Zed3 with a 5 speed.
I've also owned many MB manuals, starting with my first MB, a 190SL in 1974, and the last was a W124 300E five or six years ago.
For later MBs, W123 and up, the need for a manual moves from absolutely necessary to a depends.... By the 240D, MB had added enough HP to make the auto a viable alternative. Comparing the MB shift experience to lots of other cars most always left me disapointed in the MB action and ratios choices. By comparison, the 4 speed autos were exceptional compared to most automatics in contemporary vehicles. I enjoy manual transmissions in my cars, but I don't miss them in my MBs, and as I've aged (matured?), I find I prefer them for day to day use.
I've moved from W123 chassis cars W124 chassis cars and in my opinion, there is no comparision between them. The W124 is faster, much better handling, and gets superior mileage compared to the W123. It has all the attributes I loved in the w123, and comes with features you'd never find in a W123.
The logical upgrade from a W123 diesel is a W124 300D or E300 diesel. Not common, but they are out there in reasonable numbers.
Jim
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14 E250 BlueTEC black. 45k miles
95 E320 Cabriolet Emerald green 66k miles
94 E320 Cabriolet Emerald green 152k miles
85 300TD 4 spd man, euro bumpers and lights, 15" Pentas dark blue 274k miles
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