I still own the S55 AMG I purchased in 2001. I use it as a pleasure vehicle (Driven 1 to 2 times per week), as a partially driven car over the last 10 years it has been a pretty decent vehicle w/ it's share of problems. Overall, it's great vehicle and a huge conversation piece.
The 2001 S55 AMG is worth it, new or used. Currently own two while this is my third Mercedes. This one has an excellent balance of performance and comfort which is very hard to beat in this model. Take it for a long drive, pulsed massage, air conditioned or heated seats pamper you along the way. This car is complicated to maintain, it requires a genuine understanding of what's under the hood. Find a solid mechanic and you are set, it is a very reliable car. It is a given you need to bite the bullet on gas mileage. Stick to cruise control to save, makes a difference. Ironic advice given tempting performance at your fingertips. Scratch that, pay a little extra, enjoy the ride!
As my first luxury car, I guess I jumped ahead. But I couldn't resist when I first drove it. In and out it has everything I could want. The seats look hand made with high quality leather, which gives it a great feel to it. The V8 AMG keeps up with M ustangs (not that I've raced one...lol). If you love attention this a the car for you.