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Metal would also only work about twice if you are talking about copper. I've not seen vinyl and I think you are referring to nylon which work well again maybe only twice. At the small price they are, I'd replace them with every change.
Vinyl for me. I used the same drain plug w/vinyl gasket for 11 years on a Ford van I had and never a leak. IMO it's all about using proper torque when you re-tighten the plug NOT cranking on it till the cow's come home as so many people do.
Ive had the same plug and washer since I got the car. I think it says you should change it though.
What I do is take the washer off and flip it around. At least that way, the washer is "reset" and it gets to take on the shape of the pan and plug all over again.
Havent had any leaks and I change my oil around 3 times a year, been 7 years... or just over 67k.
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