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I went through a negotiation course about 12 years or so ago. One of the many rules of negotiation is to always try NOT to give a number. In some cases you have to state the first number. When you have to, NEVER worry about insulting the other fellow with a low ball offer. In fact, if you make it so low that he thinks it's ridiculous, then you can force him to give a number.
Don't dare bet that he gave anywhere close to the book price on a trade in. In fact if you're going to bet, bet that he got it for nothing. That's the way most trades at dealers go.
Also, it sure would be nice to know the maintenance history OR do a compression test. But, if you're getting it cheap enough, if it is worn out, you can just dump it.
My brother in law bought an '86 or '87 300D with almost 300,000 miles. I thought he was crazy when he did it in spite of the fact that the car was in pristine cosmetic condition. That was about six years ago and he's still driving it. It's in great shape to. Of course, he is a tech at an MB dealership so he knows how to maintain it and keep it going.
Good luck,
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