Error message disk/file cannot be read or written to

Every time I get to a certain point in the syncing of my itunes library, this error message will appear. Once in reference to Itunes, and again in reference to the device. It worked fine before with the same songs, and a few weeks ago this started happening so I cannot sync my entire library to my ipod anymore, only a small portion. Also many of the songs that are not able to sync will cause my itunes window to freeze if I try to play them on the computer. I have updated all my software for itunes and the entire computer, I even have bought a new ipod but the error message is still there. I am operating with mac OS X 10.7.5, and my firewall is turned off. There are some TCP ports that I think need to be opened that arent, namely 80 and 443, but i dont know how to do that? please help in clear language, I am a little worried about messing around with my computers operating system since I am not quite sure what I am doing.

See this troubleshooting article.
Disk cannot be read from or written to error syncing iPod in iTunes.

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