Customized Tags for Songs

I am a bit of an organization freak. I have been using J. River Media Center to play songs, but now that I have an iPod, I am disgruntled because when I copy the songs to my iPod, the images do not come over, and half the songs don't play.
I am trying to use iTunes now, but I cannot seem to figure out how to show custom tags. For example, in Media Center, I invented new tags that did not exist to allow me to categorize my tracks in different ways. I made a Mood tag, a Principal Instrument tag, a How Discovered tag, a Country tag, a Status tag, a Fave tag, etc. iTunes does not seem to have a way to show these tags or allow me to create them. Am I missing something?
[email protected]

But why not? It is a no-brainer. Why not provide people with the convenience of creating their own tags? I think I shall stay with Media Center just for this reason.
I know I can put tags in the Grouping or Comments field, but this is really a visual inconvenience when you have many tags. For example, I have a song that I want to tag with Piano, Norway, Faves and Upbeat for the purpose of creating separate playlists. I know I can set the smart playlist to say, "Grouping contains Piano" or "Grouping contains Faves", but visually this is an inconvenience, and when you have tons of songs you want to categorize in many different ways, it is more convenient to be able to create separate tags entirely.

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    If you drag items to the shuffle in iTunes, you are loading songs manually.  Dragging playlists to the shuffle loads the songs, but not the playlists.
    If you created playlists in iTunes, you should set up automatic syncing.  Here's how to do that...
    Select the shuffle in the sidebar, under DEVICES.  Near the top of the window, there is a bar of buttons, starting with Summary.  Click Music next to Summary.  This is the shuffle's Music screen, where you tell iTunes how to sync songs.
    Check the box for Sync Music.  Below that, choose the option to sync Selected playlists, artists, albums, and genres.  In your case, find and checkmark those playlists you want under Playlists.  You don't need to use the other lists for Artists, Albums, and Genres. 
    When you click Apply, the songs on those playlists and the playlists sync to the shuffle.  Going forward, to update songs on the shuffle, just update the songs on those playlists (add/remove songs) in your iTunes library.  The shuffle does not need to be connected.  The next time you connect the shuffle (or click Sync if already connected), the same changes sync automatically to the shuffle.
    Now, you can use VoiceOver to select the playlists on the shuffle.

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