Going upscale, W124 style.
Brewtoo, what about getting the upgrade from a W124 sedan to a really mint W124 Cabrio or a Sportline coupe?
It'd still be in the familiar idiom but really something beautiful and exclusive.
And then there is the E500/500E, you'd LOVE driving one of those, guaranteed. (or the E420, for about 75% of what the E500 gives you, but at a budget entry price.)
Not to say the W210 is a bad choice, it indeed is more modern, but it's inferior in build quality to the W124.
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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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