ITunes could not copy " song " to the iPhone " iPhone name " because the file could not be read or written.

Hi All,
Computer-
MacBook Pro
Processor  2.3 GHz Intel Core i5
Graphics  Intel HD Graphics 3000 384 MB
Software  Mac OS X Lion 10.7.4 (11E53)
Phone-
Iphone 4s Model MC922LL
14GB
-iTunes version 10.6.3 64-bit. 
-Happening since os x update 10.7.4.  No issues with os x 10.7.3. 
-It will look like it's sync'ing the song both on the mac and the phone, but it's greyed out on the phone where it shows the progress of the song coming over.  It will then give the above error after about 5 minutes.  Can't play the same song through itunes on the mac as well.  It will play for a milisecond then hang iTunes and at other times the entire macbook pro so I need to hard shutdown.  About 500 songs out of 6000 so far I've found the issue.  Doesn't seem to be any from the itunes store, just cd's I've ripped onto my mac but I'm not positive on that as I can't test all songs with the time it takes to reboot (found the 500 by trying to sync all songs and having itunes random pick them).  Also noticed that on a single album most songs will be fine but then others have the issue.  Any help would be greatly appreciated!!!
Chuck

Ok, so I dont think that I have ever been more mad at a program than I am right now.  So I had about 120 songs on my iPhone that I all bought myself, but about 80 of them were on my computer.  So I imported them into my iTunes library then I tryed to sync all my music back on; including the other forty songs.  But when I did that, all of the 80 songs wouldnt sync.  They work perfectly fine on iTunes, but they will just not sync!  I have tried dragging them into playlists and everything.  I am not new to iTunes, and I completely understand why people steal music and jailbreak their devices.  All the stupid copyright laws and sharing stuff mixed with a poorly written program makes everything so difficult!  I completely understand why people try to root their iphone and manually drag the songs on, because there isn't something saying "no! don't do that!  Even though you bought the song you can't do that!"  If Apple was so concerned with copyright, then they should really try to fix iTunes and make it easier for people to use, because otherwise, they are really turning people away from paying for their music.  I know quite a bit about computers and have been around, and if iTunes is messing with me, I am positive that it would be insanely confusing for an old person, or someone who just wants to put music on their iPod and doesnt want to deal with all this stuff that he has no idea about.  Well, sorry about the huge long complaint, but it is so annoying, and I am sure that many people will agree with what I just said!  Oh and if anyone does have advice, feel free to let me know.  Thanks.

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