Fancy URLs problem.

[yojoe]

So how do I error search this? Any specific logs that can help or any test since I haven't played around with anything like this before it would help with a hint of what to look at.

This problem is related to win+apache, not to webapplication using mod_rewrite. At least not directly.
Make sure mod_rewrite is working correctly on your software platform.
You can easily find problems, and solutions, where among the others you should be interested in "AllowOverride all" option.