Yep, a tough question indeed. But I have to throw my vote in favor of the W123 240D w/manual gearbox. I used to own an '81 240D automatic, and while it was slow and horribly noisy, with 280,000 miles on it, it still ran like a champ and never ever needed to be plugged in in the winter. I let it sit for two weeks in -20 degree weather when we went to Florida a few years back, came home and she fired right up. Now my FAVORITE Benz is by far the W116. As it has already been stated in this thread, classic styling, vault-like construction, wonderful well-balanced ride (no need for snow tires either!), and especially with either the 6.9 (which I did own as well, a '79 model which I ran up to 203,000 before selling) or the 5 cylinder turbo motor, it's a phenominal automobile. Sorry to all you new car guys, but the new MBs are way to plastic(y) for me. Frankly, they remind me of a Toyota Camry. OLDTIMERS FOR LIFE!