Question: We're deploying a new website, hosted ourselves. Short of getting in white hats how would you go about penetration testing from outside the network?

Answer: 
[Nikto](http://www.cirt.net/nikto2 "Nikto") is a nice start to look for well known vulnerabilities. Works on Windows and Linux, etc. Simple enough even for noobs like me :)
Actually i'm the main creator of a new pentest LiveCD Distro, which is a fork of Backtrack 4.
The Distro embbeds everything needed to make good penetration tests ( OpenVAS, Metasploit, fasttrack, milw0rm exploits...). Its name is shadowcircle, and you can check it out @ 

www.shadowcircle.org.

Hope you'll like it ;)