One way that attackers can find out information about a site is how well they can index it and determine your directory structure. A tool like wget can be handy in this regard. Interestingly enough, one of my students ran across this tool: IntelliTamper. This Windows tool, while not worked on since 2002, seems relatively fast and even has options to allow you to access a site using cookie information. It may be a good way to determine exactly how much information you provide to an attacker.

I did cause it to crash once (as I've said elsewhere, I'm quite good at that) so it may have the occassional burp, but otherwise, it looks rather interesting as an information gathering tool.