I found a very nice bulk rename utility (freeware) that allows you to randomize files in a folder and then add numbers as suffixes, even with separators. Very handy for renaming files and folders.
1. StepDownload Bulk Rename Utility
The tool works flawlessly on Windows 7, Vista, XP, 2003, 2008, 2000, NT. Make sure you download the correct version – 32bit or 64-bit. If you don’t know what Windows version you have read this tutorial.
2. Step After the installation use the file browser to go to your folder with all the files that you want to randomize
3. Step Click on Action – Random Sort
4. Step Now on the bottom right there is a field called Numbering
Select the Mode “Suffix” from the dropdown and enter a separator if needed:
5. Step The text “Numbering” will be orange if you change any settings
6. Step You can now click on the Rename button and it will rename the files. They will be randomized with numbers at the end.
Now you can do whatever you want with the randomized files. This is a good way to shuffle music or create a random order.