OMHO, the best way to go with this type of purchase would be to move up to the 2000 model year and look for a private party sale with time left on a Starmark warranty. Last month, in my area, there was a 2000 E320, 65,000 miles, original owner, with Starmark warranty until Feb., 2007, for $17,500. Starmark warranties are only transferable between private parties. If it goes through a dealer, the warrenty is void. That's the kind of car you want. You have to be patient and diligent because these deals can be far and few between and then gone in one day. I don't think you could find a 1999 model with Starmark warranty still valid. On the other hand, if the used car traffic in northern Iowa makes if very unlikely this will ever happen, read all you can in this forum about any issues and good luck.

One more thing: If you do end up with a 1999-2000 era MB with typical miles, the crank position sensor is probably on its last legs.

Dan

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2012 E350 Bluetech