New Ipod touch does not sync all songs

I just got a new ipod touch 32gb, i have itunes 9 on the compter. had 5th generation ipod touch orginally. itunes set to auto sync. plug touch into computer, registered it, showd itouch on itunes. first keep getting several "song can not be sync unkonw error (50). when synce is complete, touch only has 47 songs on it. i have over 1300 songs in itunes. when touch is connected, summary shows that there are a lot of songs. 7 gb. touch shows all playlists but only one or two songs in them? most songs not purchsed through itunes, most are mp3 some are aac. unconnected and reconnected touch several times and still not syncing itunes library. please help

I have an iPod Touch 64GB and over 20,000 songs. I only put approximately 7,500 songs on at a time. I have a song on 2 different playlists. It appears in one playlist, but not the other. My iTunes & iPod are both updated w/ the most recent versions. Is there anything that I can do to rectify this issue?

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