How do i randomize my playlist?

Hi I'm totaly new to ianything. Ive used other mp3 players but never used an ipod or itunes. I got an ipod shuffle as a gift and I like the player but i hate Itunes. I have 42 days of music on my hard drive because i HATE repeats and when i try to sync, itunes says its too big to fit on the ipod. Itunes asks would i like itunes to pick a selection of songs and fill the ipod. I click yes but so far it just goes alphabeticly down the first 245 songs of the library(the 2 gig shuffle is supposed to hold 500 songs but that a complaint for a different day) . I disabled those songs and it went to the next 248. Aside from setting up a different playlist every time i sync (and who wants that hastle), is there a way to make itunes randomize what gets synced? I didn't see it in the options but its possible i missed it. If not then is there a crack i can download somewhere to let windows media player work to sync the ipod? I'm using itunes 9.0.2.25.

Make a smart playlist that is only songs with a play count of less than 1, and limit the playlist to about 240 songs, selected randomly, live updating checked. When you connect your shuffle, uncheck the box that says something about syncing your entire library. Instead, sync only selected playlists, and let that be the one you select. When you have listened to your shuffle for a while, then reconnect your shuffle to iTunes, it will know that you have listened to some songs, they will get a play count of 1, so they will be removed from the playlist and replaced by new songs. This will happen whenever you sync, so you will only have songs in your shuffle that haven't been played. If you have songs that you want available, you will have to make another playlist with those songs, checking that playlist in the sync option. This will reduce the capacity for the playlist I described above, so you will have to reduce that playlist's quantity (of 240) appropriately.
I wish I knew how to paste images on this thing to show you what the smart playlist setup should look like. Perhaps someone can do this for me?
Message was edited by: duckredbeard

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