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iRank version 1.0 (beta):

(click screenshot for bigger)

iRank is essentially an extension of iTunes' "My Rating" field. It works alongside iTunes, and enables you to make any number of custom Ratings for your music.

iRank uses the comment field of your songs to store the values of your custom variables, and has an easy interface enabling you to see and change all of these variables.

It also features a boolean logic system (more flexible than iTunes smart playlists) for generating playlists using your custom ratings.

*** iRank requires the .NET Framework, which can be downloaded for free from Microsoft.

Obviously, having iTunes would also be a good idea ;)

iRank Uses the free resource Glacial Listview - Copyright Glacial Components Software 2004

iRank is currently in beta. It is capable of changing your iTunes ratings, comments and playlists - nothing more. So any damage should be limited to these at least ;)
I can't guarantee that it won't screw anything up, but I personally use it, trust it and find it incredibly useful...

Installation:

Just extract the entire "iRank" folder from the .zip file. As long as the files are kept together, it should work fine.
Also, you need to have iTunes running to use iRank.

Things you should know:

1. It's your responsibility to make sure that your custom playlists do not have the same name as an existing playlist.
   When iRank generates playlists, it will delete existing playlists with the same names (it will warn you first though).
2. Updating a custom value for a song will mean that song has to be re-downloaded to your iPod. There's nothing much I can do about this.

For operation and uninstallation instructions, see the included readme.html

Special thanks

...go out to Matt, for all his coding wisdom and help :)