Earlier quoted context omitted.
Steve Jobs driving a car for 6 months actually might increase it's value. I may be exaggerating slightly but I bet it didn't cost all that much.
I don't think most people who can afford $120k Mercedes vehicles really care who's driven them before. If it was a Ferrari driven by a rock star, maybe , but people who drive Benzes are generally boring and reasonable.
For all we know though there's some loophole that lets the dealer resell the exact same car to Jobs every 6 months which somehow keeps it under the no-plate period.