You pose a good question. Here's my long-winded answer.
It would definitely be nice to have a new Mercedes but once the car has aged I'm not sure I would be happy with it. It won't be exclusive, it blends in with all of the other 2003 Mercedes and it just doesn't have the musclecar look to it. Honestly you wouldn't be able to tell the difference between the 03 E500 and the E320.
I like the idea that our cars are owned by car enthusiasts who understand why this car is special. I love the look of the W124, the lines look great and with small changes to wheels/lighting the car is updated for at least another 7 years.
Not to mention that our cars were custom built by Porsche with the reliability of a Mercedes who else can say that!
Personally I'm really surprised that the prices of the 500E aren't higher considering how hard it is to find a decent one.
So I guess my answer is I don't think I would trade mine in either. Except maybe to sell it and buy two 500E's!