Where should I start...
Roxie - Your're up first. An AMG would be nice but trust me when I say this, maintenance is EXPENSIVE. Even if you were to do the repairs yourself, the parts are more then you can imagine. To give you an idea, we are going to replace the right rear strut on an '02 S55 AMG. Want to take a stab in the dark what the part costs? No? Try $1,700 and that doesn't factor in the labor. Although you make more money doesn't necessarily mean you should buy a more expensive car to keep up with the Jones. Buy something you can live comfortably with opposed to having to worry about dealing with a high car note, the maintenance, insurance, etc. Sure, it may give you the image that you've got money but at the end of the day, you're broke and couldn't go to the movies with your friends because you just paid your insurance. I'm not trying to preach you but rather give you the other side vs what you're friends may cheer you on to get. You're still young and have plenty of years ahead to have the "nicer" things in life.
Steve - You're just a nerd but wait, I'm the same way. lol. Everything that goes on my car is there for a reason and I've done my research on that particular part. I can't believe you're still on the original turbo at 170k miles. I have a feeling I'll be going through the motor again but have been looking at going with a Rallispec bottom end and sending a set of EJ207 heads off to EQ to let them work their magic. If I'm going to do it, I might as well go balls to the walls and do everything I want since I'll be in there anyways. Clutch is definitely on it's way out. Just waiting till it gets worse to pull the trans.