The copper gaskets are available for less than ten cents each. When I bought a mess of "Turkish Frams" at the Pep Boys sale, they didn't come with washers so I bought a handful from ******** Arizona for eight cents apiece ("Fischer & Plath, Oil Drain Plug Gasket; Copper Seal Ring 12x16x1.5mm"). For that price, even a cheap Scotchman like me can afford to use a new one every time.
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http://www.***************/search/productx.aspx?sid=sxmau3b3m0jjnmms55rf4bbu&makeid=800016@Mercedes&modelid=1193790@300DT&year=1985&cid=20@Engine%20Parts,%20Seals%20%26%20Gaskets&gid=5428@Oil%20Drain%20Plug%20Gasket
I've also reused the crush washers, but as mrhills0146 says, don't overtighten. I believe that there's a torque spec for the drain plug but don't remember the value just now. Sometimes I put a little Teflon tape on the drain plug.
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"Buster" in the '95
Our all-Diesel family
1996 E300D (W210) . .338,000 miles
Wife's car
2005 E320 CDI . . 113,000 miles
My car
Santa Rosa population 176,762 (2022)
Total. . . . . . . . . . . . 627,762
"Oh lord won't you buy me a Mercedes Benz."
-- Janis Joplin, October 1, 1970