My worst Windows habit? Indiscriminantly downloading new files and dumping screen captures onto my desktop. When things start to get too messy, I'll go on a wholesale deleting spree or chuck everything extraneous into a single folder and bury it in the recesses of my d: drive.
Enter
Deskcretary, a free app which claims to be the "most advanced Windows desktop cleanup software ever."
When you first launch the program, Deskcretary will step you through some initial setting screens - files that you want to exempt from cleaning, compression level, copy and replace policies. At the end of the process, you'll be asked to set an archiving schedule. Daily, weekly, and monthly jobs are supported, or you can turn off scheduling completely and run things manually.
The most clever feature is the Deskcretary Explorer, which allows you to browse previous archives. Jobs are cataloged by date and there's a built-in search feature which yields quick, accurate results.
I'd love to be able to change the location of the archive folder, but I'm not going to complain about the fact that Deskcretary plops it on the desktop. After all, that's where all my clutter was ending up anyway. Renaming would be a nice option, too - perhaps we'll see that in a future version.