As an S600 owner, I would advise a bit of caution.I really like the Mercedes from the 1980's and 1990's. At that time, Mercedes told their engineers to build the best most reliable vehicles without regard to cost. Many of those cars made it to 400k miles. Sadly, in the latest issue of Consumer Reports Magazine, Mercedes is now the least reliable brand of all the 25+ car makers listed for new car reliability. Also, the astronomical parts costs and dealer costs make total cost of ownership a little too high for me. I was thinking about buying a Mercedes S600 from the late 1990's where depreciation makes them affordable and the parts are still readily available.
The W140 chassis and body are bulletproof, and built to that old standard, but the M137 V-12 had a couple of serious issues. So, stick to the earlier M120 engine. Avoid the late 90s models of the W140 with the -12, stick with mid 90s. I’m not sure of the crossover year, but some time on forums like BenzWorld would be well spent.
The successor to the W140, the W220 (mine) isn’t built to the same standard. I love the car, and the performance, but I sure would like some of that old Mercedes build quality.
@JHZR2 has a couple of W140s, I think he’d be a great resource if you’re serious about one.