Date registered: Feb 2008
Vehicle: 2004 W220 (S430) ; 2001 R129 (SL500) Sport
Location: Alabama Gulf Coast--formerly Charlottesville, VA
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You are looking to buy a W108 chassis. They are one of the most handsome post-war designs Mercedes built, IMO. I owned a '72 280SEL 4.5 (W108) back in the early '80s, and it was my first Mercedes.
The floor shift was an option. You'll be able to tell the minute you see it whether it is factory or not. I can't imagine anyone going to the trouble of converting a column shifter to the floor.
The model nomenclature tells you something about the engine. A 280S has a 2.8 liter carbureted engine. It is the lowest powered W108. The 280 SE has fuel injection and has more horsepower. The 3.5/4.5 models have either 3.5 or 4.5 liter V-8 engines and are most powerful and fastest. None of the 6-cylinder models are particularly fast. To be fair, they are no better than adequately powered, but once up to highway speeds, they can keep up with modern traffic. The V-8 models cruise and accelerate with modern rides (well, most modern rides; like 4-cylinder Corollas and stuff).
The W108 isn't bad to rust, but the cars don't have the rust-proofing of modern cars, so they will rust. If the car has been in snow and salt, it may have rust problems. Someone who knows W108s better than me can give you more information about sheet metal problems.
The 2.8 motor can last 250-300k and more IF the car has been maintained properly all its life. Mercedes are engineered to last almost indefinitely, but only if they are maintained as the factory recommends. Using cheap fluids, bulk oil changers (like Jiffy Lube), non-MB recommended fluids (Mercedes usually has VERY specific fluid quality requirements, but people think they can throw 7 quarts of 10W-30 from Wal-Mart in the crankcase and be fine), and lax maintenance intervals will shorten the life considerably.
If you are very lucky, you will find a car that has extensive and relatively complete maintenance records. That is the only way you will know the true condition of the car you buy. The seller to you will likely be the fourth or fifth owner.
The W108 is a very robust vehicle, but it is not indestructible. Neglect will shorten its life just like neglect will shorten the life of any vehicle. A neglected MB will probably still outlive most other marques neglected the same way, but it will not live to its design age.
Good luck in your search.
"Don't pick a fight with an old man. If he is too old to fight, he'll just kill you."--John Steinbeck