ITUNES DELETED STUFF ON IPOD. music won't go back onto ipod?!!

So, this is the second time this has happened and I have had enough. I have about 3,500 songs on itunes and ipod right? So I decided to add some new cds to itunes, delete old music, clean up itunes so my ipod is more organized. I plug my ipod in, and I'm like okay..updating why is this taking so long?? I come back about 20 minutes later and the amount of songs in my ipod decreased it said. so im like ajghhgdjfkg not again?!!!! NO! so basically, when i updated my ipod, everything got deleted except like 100 songs, but what good is that.
I still have alllll my music on itunes, but it won't go back onto my ipod!! WHY? it does the little hold on symbol thing and says to wait, saying its updating, but its not. why won't my music go onto my ipod, and more importantly WHY DOES THIS HAPPEN EVERYTIME I PLUG IN MY IPOD?! last time it took like 6 hours just to get my music back on. HELP!

With the iPod connected to the computer, go to the File menu in iTunes and choose Transfer Purchases from (iPod's name)
CG

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