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S500 is probably the best choice, '97-'99, but these are pretty complicated cars.
The AC can be a horror if it goes out, back at A Mercedes Benz dealer in Santa Rosa in 1997 I saw one in the shop, the entire dashboard and both front seats had to be removed to even get at it.
Book rate at the MB dealer for this was - hold your breath - 22 hours!
Soft close doors, dual pane glass, the cars tried to out-Japanese the Japanese with these, and a bad one can be a money pit.
I would only buy one that had ALL books and records from brand new, and was lovingly cared for by an anal, picky owner.
The ultimate catch would be to get one of the 700 "Grand Editions" -- the last of the w140, a special edition tribute model (1999 model year only) -- all were gloss black in color with AMG wheels, bird's eye maple trim, special floor mats and other goodies.
Yeah, for me it'd have to be a mint '99 Grand. Every one of them had the 500 engine, which considering the size and heft is just about the right size, the 600 12 cylinder being over the top, and a potential nightmare in repairs.
The worst of the bunch would be the first year, 1992, in V12 guise.
Plus the build quality was still excellent - it went downhill fast with the 2000 w220 models that followed.
And the w140 is really really safe! Nevermind the Princess though - her w140 was a salvage title rented s140 280SE euro from a French limo company and that vehicle that was a lemon, and a repaired wreck. AND she did NOT wear her seat belt!!!
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 1991 560 SEC AMG, 199k <---- 300 hp 10:1 ECE euro HV ...
1995 E 420, 170k "The Red Plum" (sold)
2015 BMW 535i xdrive awd Stage 1 DINAN, 6k, <----364 hp
1967 Mercury Cougar, 49k
2013 Jaguar XF, 20k <----340 hp Supercharged, All Wheel Drive  (sold)
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