Date registered: Jan 2010
Vehicle: 1995 E320 Wagon
Location: Lakewood, Colorado
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Over the years I've owned a 1958 219 and a 1959 220SE sedan and driven them well over 50,000 miles. For a while, in the 1980s, the 220SE was our everyday car, and I wouldn't hesitate to recommend owning one. I'd want a 220 though, not the less powerful 180 or 190, and the fuel-injected SE has significantly better performance than the carbureted S (starts and runs better, too).
Good points: relatively inexpensive to buy and maintain, more interesting and different from the ubiquitous SL models, useful, and they have a certain charm. Drawbacks: not the best brakes or heater (what air-conditioning?), go only about 100,000 miles between valve job (usually it's the guides that wear), the Hydrak clutch can be troublesome (but can be converted), and a good older mechanic helps a lot.
As usual, rust is your enemy. For more, see my book, The Illustrated Mercedes-Benz Buyer's Guide.