Also, be cautious of the R230 models with the early years of the 7 speed automatic transmission; as the first few years of the 7-speed were problematic.
If I were you; and assuming you don't need the fire-breathing AMG version, I would find a R230 SL350. The SL350 wasn't available in the USA, but I'm told in Europe, they built SL350 without the ABC suspension. I wouldn't own an ABC suspension vehicle if I could avoid it.
Another thing to consider is a CLK55 AMG, these vehicles are very simple and reliable; and they meet your 2 door requirement.
If four doors ever was your style... Get "Le Beast" the 2005/2006 E55 AMG. It's a fire-breathing monster! Easy to maintain! Very reliable!