ITunes & iPod music question?

So I got a new iPod (4th gen if that matters) and I have over 3 thousands songs including over hour long mixes so it takes a LONG time to put all the songs on my ipod. I've been at this for like 3 days nows (putting music on my iPod) and i've just hit a wall. I didn't sync my ipod to put on all the music that I have on it already, i just Shift+A all the music in the library then drag & dropped it on the ipod. But now it stopped working? (fml) So I was looking what was wrong and noticed i wasn't syncing with my iTunes. I'm only a few songs (800+) short of having all my music on my iPod. So I was wondering if I tried syncing with my iTunes will all the music already on there be deleted & the process restarted? I don't want that. ._. takes too long. any other solution?

Ok. Does that script work instantly? I waited a bit and then when I clicked in itunes, Script Editor told me something like "Itunes had an object error".
Then I checked and there are 3110 checked songs in my itunes library and only 2696 on my ipod. Why is this?

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