I own a Mercedes specialty shop on the east coast. We do everything from mid-50's to modern. The old stuff is cool, but the prices some are commanding now are insane in my opinion. I owned a 500E for a short time that I purchased from a customer when I first opened. I sold it within a week for 4x what I paid and reinvested the money into the shop. The green convertible in the pic was purchased for $250k. The white car is an original Hammer 6.3, unfortunately the customer didn't have the money to get it back into good condition. The last pic is about 4200 hp of modded cars we have done for customers. It was a weird coincidence they all ended up at the shop the same day together.
As for my favorite the CLK Black was very high on the list, I'd have to dig up pics of that one. The 1 of 5 CLK GTR roadster I saw at a friends shop was insane also. My personal favorite at the moment though is my S63 coupe tuned to about 750hp. It just does everything well and is unbelievably fast in everyday driving