I've done a search and have found some good input on this subject. While it is concluded that the 80's 240D is the most reliable with the least amount of problems, at the same time I feel that if I am to invest in a diesel then given the savings on the diesel, I'd like to go with the bigger body benz.
with that said, what models should I search for ?
I don't want anything too problematic like the W140 body style with the diesel.

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Whether you think you can or cannot, Either way you're right!. by Henry Ford.

Benz 300

all I remember is when the Turbo Diesel first came out the main bearing crank seal would leak due to vacuum created by turbo. I think it distorted under full Turbo boost and the oil pressure would let a little motor oil past the seal under this brief distortion only at full boost. The women never checked the oil and many failures due to no one checking the dip stick. I think the beefed up seal went on in 1985. I think if you just check the dip stick more than once a decade you will be fine with models prior to '85. I had a 300D 1981 non turbo that year as 82 brought in the Turbo and only had climate control issues and rust right behind the front wheel and real wheels. My 81 had the fast glow plugs which meant you did not start at 0-F unless you had Mobil One in it and had to hold glow plugs for 45 seconds after light went off before a start. My brothers 1976 300-D with old/slow plugs would start in the cold , with no problem. His 76 had no freaking climate control and far better view when you backed into a pariing space. That '76 was his favorite and between me, my brother and parents we all had 81's to compare with. Due to lack of power I would forget the 240 and go 300 but the 240 did come over with a manual which I would opt for if found. All 300's came automatic only.

blairbuc:
300D's did come w/ stick shifts, just not usually in the US. I have seen a bakers dozen 4spds for sale and only one of the coveted 5spds. All non-turbos, as MB never put a stick in turbo w123 because of too much torque.

Benz 300:
I have owned many diesels (mostly w123's + one 115 and a 126) and loved everyone of them for their ease to work on and reliability. If you don't like the w123 for what-ever reason, the 300D 2.5 w124 is a pretty decent vehicle. I have two friends that own one and we've never had any real problems in a combined 360,000 mi.
I also loved my w126 300SD. Either you love that vintage of big-body or you don't, so there is not much explaining to do other than to say that I would not call the this heavy turbo-diesel underpowered.
I see you are a fan (or at least have a few) of the 201 body and the 190D (in both large and small engine varieties) are spoken of as very reliable, very economical, never die cars. (And I hear the 2.5L 5spd has a bit of zip and gets in the 40's for mpg, but I have never owned one, although if I found one w/ a good history... You might have a fight on yr hands for it.)

Goodluck!
-Matt-

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Currently:
1972 350SL Euro 4spd
1973 BMW R75/5
1981 BMW R80GS
1995 FZJ80 with OM606 Conversion In Progress

i may be biased, but i dont think theres a better all-around diesel model than the 85 300SD...its certainly big enough, has plenty of power, and can cruise all day at 100mph and never break a sweat( i do it all the time in mine)...the key to buying any car is to be sure its been maintained well...i got lucky, my grandfather bought mine brand new in 85 and it went through him and my mother and then finally to me a few years ago...its always been kept under a garage, been maintained very well....the only gripe i can come up with about my car is that damn squeaking MB Tex interior, which will be all leather shortly

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1985 300SD 192,000miles...Astral silver/ Grey MbTex

1983 300D 194,000miles...White/Tan MbTex...my newest addiction

If you don't live in the rust belt, definitely get a '78-'80 300SD. Ask anyone who's driven both, and they'll tell you that the 116 is faster and most would agree they drive better. I redid the front-end on mine and hate keeping it under 100. Find one without rust that's been taken care of and you'll never want anything else, I guarantee it.
Thanks
David

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2000 Honda Accord V6 137k miles

1972 300SEL 4.5 98k miles

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Oh, what the heck. I'll throw in a vote for the SDL. Heads crack once, valve adjustments are forever

The SDL has engine electronics but only to control idle speed and emissions. An SDL in decent tune can idle with the ELR disconnected. You can manually raise the idle speed if you're going to be without ELR for a while.

Sixto
95 S420
87 300SDL
83 300SD (sold)
81 300SD (sold)