I'd say the 911SC coupe. They have rock solid durability, a marque with a large following, good racing history, and the parts are readily available. As with any collector car, it should be the nicest car one can find.
I didn't see the E30 M3 thread, but this M3 is my favorite BMW.
I don't see the Datsun 240Z doing anything. They just never caught on with the collector car crowd. The only year that is popular is the first year (1970).
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Mercedes Benz 190E 2.3-16V
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It's rated a "F" in the SCM price guide. Can you still buy the Cosworth parts?
I don't see the Mercedes and BMW M5 sedans as ever doing well. The are complicated and expensive to work on, not rare, and not particularly attractive. JMHO, of course.
I think a low grill MB 280SE will do well.
A Ferrari 328 GTB and 328 GTS (1986-1989) are going up. The F355 series (1994-1999) have almost bottomed.