If I were looking, $5,000 buys tons of well kept early W202s, much car for very little up front cost. The C220 M111 is OK, and the M104, even with its problems, is a sweet engine. An often forgotten problem with the early ones, at this point, is the ACC system, though. Keep in mind that the W202 is cheap, but is still very much a Mercedes... If you have to pay a specialist to keep up with every little thing, you're in for a rude awakening.

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Michael

1988 300 SL (5 Speed)
1994 E320 Wagon
1997 C230