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1996 SL500 that I stuck with for ten years/100,000 miles.
Take a car designed in the mid-80s, then graft on OBDII and an early CANBUS so nothing really communicates well. Throw in a mfr and dealer network who was thoroughly indifferent to supporting their “timeless” product, an owner community that preferred to let others deal with repairs, extremely clunky diagnostic tools involving a multiplexer and a laptop with a serial port, etc.
Between initial purchase of a good 70,000 mile example, parts, sweat equity, and the loss I took in the final selling price, a 911 would’ve been comparably expensive and much more fun to own.
Never putting my own money into another MB.
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