Let's see if anyone else would join me.

If MB still makes and sells the 1991 - 1992 300E new today for $50k, I am in for 2. It might need a head gasket but that is only about a costly service of the new cars.

Newer cars breaks down more often or they just limp home or stay at the dealers, LOL.
Newer cars cost more to diagnose when they break down.
Newer cars rust more easily (compare W210 to W124 to 1993).
Newer cars depreciate much more than the older new cars (early W210 price is approaching later W124 now).

In the mid 1990's, one buys a 5 year old MB for about 1/2 the new price. Nowadays, one can buy a 5 year old MB for about less than 1/3 of the new price. For example, many 2002 E320's are in the low and mid teens in price they cost more than $50 new with options. The market knows what is good and not so good.