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You said you're an AZ native? Is the car in AZ?
If so I could help you look it over. (I'm an ASE master certified tech by trade and a multiple Benz turbodiesel owner as seen in sig) Especially if it's in Phoenix area- that would be easy.
As for your questions: The oil is supposed to be black (my 300SD would turn it black within 10 minutes of the oil change)- the soot in diesel combustion, for lack of a more technical explanation, colors the oil.
It's not supposed to leak seriously though. A little seepage is normal, but my SD leaked seriously, and it also lacked power (I believe blow-by was pressurizing the crankcase beyond what the ventilation system could handle in my case) whereas my 300TD has no leaks to speak of and whistles along at 85-90 mph with ease.
I'll let others jump in as regards the other questions but it sounds like this car may be a little tired. Just my off-the-cuff answer...
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1985 300TD
1984 380SL
1983 280SE (full Euro, trunk triangle and all!)
Formerly owned:
1986 420SEL
1984 300D
1983 300D
1981 300SD
1976 300D
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