Isn't a new Jetta TDI over $20k to start? You could probably buy two or three nice 300SDs or 300Ds for that price. With that being said, a new TDI will have many more safety features and will probably offer just as much if not more reliability. There is also the added bonus of a warranty and if I'm not mistaken, VW pays for servicing for the first few years of ownership.

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1989 300CE