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.
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.