OK, Tom, I get the picture.
First, consider whether you want a "car" or a classic.
You currently drive a "car", perfectly reliable, safe and comfortable.
A M-B "car", and a pretty good one at that, would be a 300E or E320 from
1987 on. This is a standard four door sedan with a straight six engine, four speed automatic. Some of these were built with all wheel drive, an option to have only if one really needs it, IMHO.
I own a '97 E320, it's a nice to drive and a fine freeway cruiser. These can be bought for as little as $12K and as much as $22K depending on condition. Always try to buy the newest and best quality M-B that you can find and afford - for cheap M-Bs are a fool's bargain. The high repair cost of bringing a beaten car back to a reasonable quality standard is too high. All that said, I'm sad to say that a used M-B will have more repairs and repair cost than a Honda or Toyota. Owning a M-B is an indulgence, like having a trophy wife - glamorous but expensive.
The second path to consider is to buy a classic. This takes time and knowledge and one must be an enthusiast to justify the cost. Something like a a two seat roadster 450SL ('73 to '80), 560SL (mid '80s) are popular, hold their value relatively well and typically have lower mileage than their sedan siblings of the same age. These two seaters have V-8 engines, another version the 380SL (early '80s V-8) is underpowered, IMHO, for the car's weight.
Old sedans are another area to consider but that subject is simply too large for this note. Some of these old classics are pretty simple others are overly complicated and therefore very expensive to have repaired. I assume by the cars that you now drive, that you, yourself, don't repair and maintain your cars, if that's true then a classic may not be the right choice for part of owning an old car is to tinker with it! I own a '80 300SD, bought new, a larger turbodiesel sedan whose old technology is all mechanical, relatively simple and can be repaired and maintained by an owner.
I hope this frames the issue, also see
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and look for prior models in the site.
Tom