But that is what I mean, what do you think those mad skillz are that are the differentiator?

Try running Nessus against it.
http://www.nessus.org/nessus/

I'll second ISA 2006, but it's real strength is front-ending MS Web servers and services (OWA, Sharepoint, etc).

It depends on the goal, sometimes part of the test *is* to trigger the logging and see if anyone is paying attention behind the curtain.

Building a dictionary and using that is very handy and is a good first pass. Straight up brute forcing over the network isn't usually effective, but it does work sometimes. Obviously it is  more effective (attempts per second) when you can hammer on it locally (e.g. file decryption).

The nice thing with brute forcing is that it doesn't take a lot of babysitting. You can let that thing run and monitor it for success.

What is the mojo that separates the good from the great in Pen Testing/Ethical Hacking? How do you know the difference between the two?