From what I understand, I need to go in the properties of the file, then the "detail" tab and set the rating there. Is there a faster way to do this?

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You can rate them in bulk in Windows Media Player (a bit different than this on Windows 7, but fairly similar):

  • In the menu select File -> Add to Media Library and choose what you want to add (probably a whole folder of media)

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  • Let it add all your files

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  • Navigate to the Media Library to see the media you've added and select what you want to rate from the imported media (All Music, All Video, etc)

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  • You can then Shift + Click (sequence) or Ctrl + Click (1 at a time) the files you want to rate. Then right click and go to Rate Selected Items and choose your desired rating.

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I assume that for images, I should use Windows Photo Gallery? – JcMaco Dec 1 '09 at 22:25
Yep, the same highlight and rate method can be applied there! – John T Dec 1 '09 at 22:52
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