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I've owned an E30 M3 since 2000, I wouldn't say the engine isn't especially hard to work on. I wouldn't really like to have to do a timing chain, but it's not bad.
I got my car for $11K back in 2000 with 125,000 miles. My car isn't worth that much now, since it has 195,000 miles, I don't think I'd be able to get more than $15,000 for it.
If you'd really want to make money on it, I wouldn't DD it. The more miles it has, the less it'll be worth, plus the E30 M3 isn't super cheap to maintain like normal E30s.
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