Image wise, definitely the Benz. Pull over on a stock but well maintained Benz, people would still somehow look at it as something really expensive.

Reliability and overall practicality, the Cefiro wins it. You can get your parts without costing you a testicle. And the parts are way more abundant than the Benz.

If I had the budget to go "all-out", no second thoughts I'd get the Benz. It's different to drive around a restored car that was once considered as something really expensive.

By the way, looking at other Mercedes Benz units the C220 seem to fit your budget ( under 350k but over 300k )

One more thing, while looking over the ads I saw this one ...





Being sold for 370k. It's a 1991 5-series BMW.