Take it from the owner of a 2001 E320 and 1999 E320 4M wagon...the wagons are great! Definitely go with a AWD 4Matic. The E-class cars are super-stable at speed, handle great, and feel ultra comfortable.

Model year 2000 is not a good choice (problematic SRS sensors, etc.); I would personally go with a 1998-1999, 2001-2003 W210.

Both the 1999 and 2001 have had identical issues: MAF, catalytic converters, window regulators, leaky rear axle.