Missing songs and transfer issues

I know i'm not alone asking about why songs are mysteriously missing and most can be tracked down manually. Why does this keep happening? Its getting worse every time Apple releases an update. Does anyone have any suggestions on why or how to fix this irritating matter???
Now that i'm over the rant, heres my main concern. I have quite a few songs that will not transfer from itunes to ipod. I recently bought a new 120g Classic to replace my failed wheel 4th gen Nano. I 'm attempting to transfer the library and it seems like everything I have ripped from CD's using itunes has at least one, if not two songs from every CD that will not transfer.
These are the errors I get when the files refuse to transfer.
"Attempting to copy to the disc " " failed. The disk could not be read from or written to."
"iTunes could not copy " " to the iPod " " Because the file could not be read or written to. "
None of the songs that I have purchased from iTunes or emusic or other sites give me this error, only files that were ripped from CD's. Any help would greatly be appreciated.

I really hate saying this but itunes seems more like a Microslop program than an Apple program. Every version gets buggier and buggier all the time with no fixes, just another crappy version that makes the previous one be better.
I haven't had much success in finding what it is that itunes looks for when it rejects the said file. I thought maybe it would be silence or scratchy sounds but it seems to be rather vague. Only thing I have found to do is create a "reburn" playlist, burn the list to disc, delete files and re-import. Or simply redo the disc import.

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