Songs on Ipod (1800) not syncing with Itunes.

I really am unsure of where to post this topic so forgive me if this is the wrong forum.
I have an 8GB black Nano, it is a little over 1 year old. Recently I bought a new computer (Windows Vista.) I can't remember if this problem started right when I got the computer or when I updated my Itunes. I have a problem where my 8GB has 1800 songs yet when I plug it in to charge in my itunes only 110 songs show up (my purchased from Itunes material.) Downloaded songs and songs ripped from CD's that I own do not show up. Moreso, I can not add any more songs to my Ipod. For example, I downloaded two songs and they are in my Itunes (and yes the box is clicked) yet when I plug in my Ipod it won't "sync" or anything. I've had this problem for a few months now, and I don't know how to fix it. Listening to the same songs over and over is driving me insane. So if someone could please help me fix this problem I would really appreciate it!!
thanks!!!

because i’m not syncing itunes with my ipod there is no way to transfer these covers automatically on the ipod.
If you are manually managing the music on your iPod then adding artwork directly to the songs on the iPod (when looking at it through iTunes) has to be done er......manually!
There's no program I know of that will add artwork to the songs directly on the iPod without first adding it to them in iTunes and then transferring the songs to the iPod.
One note of caution. If you add artwork directly to the iPod, the artwork can sometimes not be displayed correctly when playing songs.

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