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If I were driving 800 miles a week, I'd want something with better fuel economy but that's just me. A newer (in both years and miles) Benz will cost more up front, yet have its own issues, and be harder to work on because there's more stuff to get in the way. I can do pretty much the same things to my '87 (W124, OM603) as I can to the '85 (W123, OM617) but when you get to the '96, all that electronics can be mighty hard to diagnose and expensive to replace (you are rarely able to "repair" those electronic modules).
All that said, my '96 has been very reliable (260,000 miles). Your car at 220,000 miles is not really a "high mileage" diesel Benz.
This is a decision that we cannot make for you but we can advise you on the estimated cost of repair, be it do-it-yourself or pay someone, if you will share with us the "issues" that your car has.
Jeremy
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"Buster" in the '95
Our all-Diesel family
1996 E300D (W210) . .343,000 miles Wife's car
2005 E320 CDI . . 148,000 miles My car
Santa Rosa population 177,300 (2026 projected)
Total. . . . . . . . . . . . 668,300
"Oh lord won't you buy me a Mercedes Benz."
-- Janis Joplin, October 1, 1970
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