Over half of my music was deleted when I got a new comuter

So I got a new computer, and no longer needed to use my parent's for putting music on my iPhone 4. I synced it to my new computer and over half of my music was either removed from my phone or rendered useless. So, I thought it was because of the music not being on the new computer's library. So I got a flash drive because most of the music had been purchased from iTunes and transfered it over. After about a week the same thing happened again when I added a new song on to my phone. Most of them would still show up as selectable, but if I chose them it would wait a couple seconds then cycle to another song and repeat until it reached some song that it had decided not to delete. This is over $100 of music that I simply can't use anymore, and I have no idea why. Can anybody help me out?

Back up the library on your parent's computer to a portable drive. Copy that into your new computer.
tt2

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