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 :)
[Free Nikto, Nmap, OpenVas vulnerability scans available online from this website](http://www.hackertarget.com)