Great post, thank you.
Yes, I drive my car a lot, and know it inside and out. I can pick out any little thing that might be wrong with it. I am concerned that it'll take a while before I get to that point with a new car, and because of that I won't know when something isn't quite right immediately. Oh well, I guess I'll just revert back to beeing a nOOb for a while.
Believe me, I will do a TON of research before buying. I've acutally been lucky enough to have one of the local Denver guys respond to my PM about chatting with him and some of the other local guys about what to look for. Not to mention all of the archives from this board and Rennlist that I have save in my favorites.
As far as buying another Audi....well, I've thought about it. Keep in mind, my car right now is every bit as fast as any generation S4 was in a straight line, and corners/brakes much better. Also, I've driven a few S4s with larger turbos, coilovers, etc. Yeah, they're fun, but they just weight a bit too much for them to be as nimble as my car. Hence, the search for a Boxster.
There's not much incentive for me to get another Audi unless it's something like an RS2 converion Coupe Quattro or similar. But then I just get into more maintenance, which is one of the primary reasons for jumping ship to a newer car with fewer miles.
Don't get me wrong, I don't race competitively. I just like to get in a couple/few track days each year.