I've owned my 88 300CE for 11 years now (I think), and last year it failed the mot on a bit of rust on the chassis, and corrosion on the brake pipes, which required the rear axle being dropped to replace. Other than that, it has only failed two previous mots in my ownership, both times being corrosion of the rear (genuine MB) exhaust sections. Straight through this year though, with no advisories, as a good rust repair was carried out last year.
Other than routine servicing, I can't think of anything extraordinary that has been done to the car. I replaced the distributor cap, rotor arm and ht leads a couple of years ago, and that's about it. Head gasket is just starting to weep a bit of oil at the nearside rear of the engine, which I believe is common, but at 144k miles, I can't complain. Garaged until three years ago, it now stays in the elements, sometimes unused for a month or two at a time, but starts on the button always. It doesn't have a pedestrian performance, but perhaps does need a bit of winding up by comparison to the later 104 engine, that's if you want to be thrashing a 19 year old engine. Even so, it was built to take it.
The only rust I have on mine is about a three inch strip at about 10 o'clock on the n/s/f wing, everywhere else being fine, and the rear screens suffer with delamination. I love it!