My MB experience has been with the C-Class. The 220 is sluggish but I still love it. I'd recommend the 280. Although I've heard the new little "Kompressor" 230 runs like a rocket.
My friend paid $22 K for a 92 300E a year ago.. I paid $22 K for a 95 C220 2.5 yrs ago. He's had LOTS more hassles with his, although he still really likes it. Locks problem, a/c problem, needs new tires. Plus, the darn thing is OLDER and it seems like it, too.
As for mine, I've never had a problem with it. Had it for near 3 years now.
No matter which Benz you buy, if you're like me, you will never drive anything else.