Date registered: Mar 2006
Vehicle: 1997 E420
Location: Fort Wayne, IN
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Look for an E320 4matic. Outstanding safety record, all wheel drive for winter driving (if that is a factor in your area), not so big as to be hard for a new driver to manage, relatively inexpensive to insure.
Depending on your definition of "expensive", they can be found very reasonably. You can find very nice '99s & '00s for under $12K all day long.
Stay away from pre-1997 4matics, though. Terrible reliability.