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I'll have to admit that I'm not a fan of diesels, so I'm laying my cards on the table, and you'll have to excuse me for my bias.
Knowing that his wife drives with a lead foot and that her last car was a BMW, I can't imagine that if she has any input at all, she would ever want to own an older MB diesel, especially a 240D.
I know that diesels get better gas mileage than the combustion engines, but the maintenance and repairs that a 20 year old car will feasibly need has to be enormous. Even if he finds one that is a cream puff, it is still likely to need more than normal reconditioning than a late eighties to early nineties MB.
After reading all the posts (without him laying down a budget), I say with a reasonable budget, he should get a W124 or a 94-95 C class, or a Volvo (240 / 740 / 850 model). You get a car that has reasonable power, a good reputation for durability and longevity, and crash worthiness (it appears she needs it).
Respecfully,
Paul S.
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Paul S.
2001 E430, Bourdeaux Red, Oyster interior.
79,200 miles.
1973 280SE 4.5, 170,000 miles. 568 Signal Red, Black MB Tex. "The Red Baron".
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