Here is my initial submission for this contest. The suite is fully functional and has performed well for me (I just cleaned 400+ MB of temporary files from my development machine).
The "Development Cleaning Suite" (DCS) is a utility that provides a cleanup handler for Widows 2000 and above. Additionally, the suite includes a configuration tool as well as an independant host (DCSUtil) for the handler - providing for additional benefits and more advanced features.
You can download the installation and a PDF file explaining everything (8 pages) from the bottom of this page.
I won't start on help files until the tool is finished due to major screen changes.
An example of its presence with the Windows Disk Cleanup Tool:
Clicking the "Review" button shows a detailed view of all files found and allows you to indicate which files should / should not be deleted.
Using the DCSUtil to perform the scan/purge
Here is a screen shot of the configuratorNote: Although I have thoroughly tested the provided tools please test carefully. By default, all deletions are sent to the recycle bin.