I previously owned a 2016 S coupe and switched over to a new Audi S7. It's a great car, and each has its strengths and weaknesses relative to each other (there are a few things the Audi actually does better), but I sometimes find myself missing the overall feel of the MB.

I'm toying with the idea of finding a facelifted (2018+) S560 or S63 coupe, ideally CPO, if the options and price were right.

As they have been out of production for a couple model years, and as I would likely be going backwards a couple of years (in regards to perhaps not quite as good driver assistance or other tech in a +/- 2020 S560 / S63 versus a 2023 S7, and getting a car with some tens of thousands of miles on it, much more than the Audi): would you do this or think it completely foolish to do? I've thought of going for one of its competitors still in production, like a BMW 8 series coupe, but I didn't love it when I test drove it, and again, there's something about the overall fit and feel of the MB.

With the recent market forces pushing towards SUVs, there just aren't many good two-door coupe options in this segment. Not confident that a well-optioned CPO E coupe or a new CLE would quite tick all the boxes.

 

Exi,
I purchased a 19 S 560 new and it has been an amazing, trouble free car. I will NEVER sell it.
A sports car it is NOT. But, on the highway, long distance, high speed drives it is great.
It is a comfortable and quiet highway cruiser.
In addition I have had many compliments on it's design and presentation.
Love it!!!

 

I traded a Jaguar XKR-S coupe for my 2020 S560 coupe and could not be happier. The Jag performed better on the track, but I only did that once. So for everyday driving, it is awesome. The tech is good as far as what you really need, including Apple Carplay.

before

after

 

100% -- not a sports car, just too heavy, but man o man is it the most amazing grand tourer. Miles just slip away and one always pops out feeling fresh!

 

I love the look of Audis but they are notorious for electrical issues at the very least.

I had a VW Phaeton, essentially an Audi. That thing lit up like an arcade game everytime I got in it. I would cross my fingers every time I entered it. Flickering lights (all lights interior and exterior) some sort of lighting module. Failed air ride suspension which the dealer stated had it not been in warranty it would have cost me $11K. Thermostat. Power window module the list goes on and on. This was at 40K miles.
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I had an Audi Q7. Similar situation always some sort of electrical issue. Battery drain constantly no one could figure out why. Finally someone said it was the trunk latch. $1000 to repair that and the battery continued to drain. Of course the battery and alternator were also replaced.

Anyone that I know that has owned an Audi has had issues. Go with the Benz. They are not without issues but they're the sort of issues you expect from an over engineered car.

The Audi on the other hands feels like they buy electronics from Temu.

Aside from that, no one makes an interior quite like Mercedes which is why I always return even after trying other cars and I have a long list.

Jaguar XJL
Lexus LC 500
Porsche Panamara
Volvo S90 T8 Inscription <-- Sleeper really impressed me
Acura CL Type S
Audi Q7
VW Phaeton

​And a ton of Mercedes, yet I always end up back at Benz. In fact I traded my LC 500 to come back to my S550 Coupe so this is actually my second and I never buy the same car twice. Take that for what it's worth.
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If you are willing to buy used or CPO there are some nice coupes that depreciate prices. Not much demand for 2 doors so the prices drop. A S Coupe is a great value used. A S560 or S550 provides amazing performance and quality.