I have a 1998 Mercedes S420 and my old 1990 Volvo 240 that I have had since new. I bought the Mercedes thinking thatI needed a newer car. The Mercedes has too much Chrysler in it. It isn't the smae Mercedes like my father's old 1881 300 Diesel. The interior feels plasticy. All of those electic options are just more things to fix. My Volvo has 230K miles but I have redone the suspension, and put new black leather to replace the old charcoal fabric. I hade the guy add some more foam andhe did some rigging with the seat grid. Feels perfect. It could use new paint I suppose. It is exciting to think of all of the money I will have to really fix it up. But how much "fix up" is too much? My insurance company would not pay me crap if the Volvo was totalled, but I guess it is much cheaper that spending several hundred dollars to replace the "automatic door closers" on the Mercedes- HA
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1990 240- 230K- IPD cam, springs, bilstiens, 3''exhaust, euro lamps

When you use words like "feels better" the answer must be subjective. An Armani "is" better than jeans and a Tshirt, but I know which I'd be more comfortable in.
My father traded in a low mileage 850 with no problems for a clean '91 245. He had a two-page list of stuff that he thought was better in the 200 series. Much of it was personal and subjective, but the fact remained, the 245 was a better fit for a lot of reasons.
It may be an anachronism, but he prefers it. As do I.

The 1998 S420 you have must be the the W140 chassis M-B. I think the W140 is the last of the true big-bodied Benz of yore. They are expensive to keep (and buy), but you get one hell of a car! I absolutely love the W140 S-Class, more so than the current S-Class. It's a pity that you want to get rid of it. I think the 1995 to 1999 W140 had all the little and big things taken care of, so the 1998 model you have should be somewhat trouble-free. Having said all that, YES, I do think you are crazy!

M-B was making cars in 1881?

someone on BB was ALIVE in 1881????