ITunes Freezes, Won't Sync With iPhone

I am relatively new to the Macbook family. Since I have purchased my Macbook air, the only complaint I have had is with iTunes. I have every upgrade that has been pushed out. The problem started when I first imported my library from an external hardrive, nothing would copy over, I reformatted the drive to work better with the Macbook and lost 8000+ songs. No big deal to me because it was time to clean a lot of the collection out. Now the external hardrive is fresh and formatted correctly. I have changed my library location to the hardrive and my music will show up in the library and play. However, it freezes all the time. The other issue I have is when I try to sync my iPhone 5 nothing will copy over, it starts then just gives me a message that itunes could not copy to iphone because the file could not be read or written. It makes no sense to me since all the files will play. Not sure what to do, I've done a million searches and nothing. I hate to say it by my iTunes, external harddrive and iPhone all worked flawlessly on my Windows machine. Any suggestions would be appreciated before I make a call to Apple Care.
Thanks!

http://support.apple.com/kb/HT2292
http://support.apple.com/kb/TS3219
google is a wonderful thing

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