ITunes acting weird

I am using the lastes version of ITunes Version 9 2 0 6 1 ...I have not actually used it and played any music for awhile now, I have not changed any settings (preferences) within ITunes. I have just tried playing some music, when it is set with the shuffle "off" once the first track is finished it does not play anymore tracks and when it is set with the shuffle "on" once the first track is finished it goes to another artist, but then plays all the tracks for that artist instead of shuffling different artists.
I hope this makes sense.

iTunes won't sync changes to the playlist over to the nano as soon as they're made, even if the nano is connected. It lets you make a lot of changes at once, then it syncs them when it is told to.
Ways to tell iTunes to re-sync the nano:
1) re-connect the nano.
2) right click (or control click if you have a 1 button mouse) on the nano in the iTunes source list. when the pop up menu appears, choose update.
3) Bring up the preferences for you iPod. Make a change. When you hit OK, iTunes will sync the change to the iPod.
Right now your nano is set to sync to specific playlists, and iTunes generated one playlist that is filled with enough music to fill your nano. If you want to drag individual songs into and out of your nano, you'll want to change the preferences to manually manage the music on your nano.
Generally, syncing to specific playlists is fine. But the playist that iTunes generates may be a problem. Since it is a regular playlist, it isn't size limited, so you can easily fill it with more music than your nano can handle. In your place, and I was in your place when I got my nano, I would replace that playlist with a Smart Playlist that is limited to a specific size in GB or MB. The Smart Playlist will never get too big for your nano.
The smart playlist that I use grabs random songs where Play Date is more than 3 months old. That way the music I listen to automaticly comes off and is replaced with something that I haven't heard in a while. I like variety, so this works for me. YMMV.
Doc

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