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: 
[McAfee Secure](http://www.mcafeesecure.com/us/) offers a pretty decent scanning service that will look at the web server, network, and the web site itself in an automated, on-demand way. Their scanner is certified for PCI scans, so it's pretty comprehensive.
[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 :)