ITunes sync problem: file could not be read or written

I am running itunes 10.5.2 on OSX 10.7.2 on a 2.53 GHz Intel Core 2 Duo Macbook
A week ago i did a so called "clean install" on my Mac, making sure to back everything up on one external drive, and clone the disk on another before beggining. I started with snow leopard and then installed the upgrade from the app store. I then reinstalled all of my software, loaded my photos, setup my preferences and devices, and finally directed itunes to the media folder on my external drive.
I had been using the external drive for itunes for a couple of years: on the previous system and even my previous desktop, with no problems whatsoever.
All my songs apps etc. showed up and there seemed to be no issue.
Then I tried to sync my iphone 4s and it started off okay, but about halfway through the message "could not sync ___ song to iphone because the file could not be read or written". When i located the song in question it was where it should be and even played properly in itunes. The second try would bring about the same error only with a different song. This went on several times before I realized something was really wrong.
I made sure to change the permissions for all itunes folders, music folders, even the external drive itself to have read & write permissions for all fields, and checked the box to include all internal files. I also tried resetting my iphone, syncing through another usb port, and running permissions checks on the main drive.
Thinking it could be a broken hard drive, I tried moving my aperture folder to the internal drive and all 30 GB transfered no problem. But when I tried to move the itunes folder to another drive, it stopped midway through and the finder gave me "error -36" saying that some song could not be transfered because "the file could not be read or written".
In case it helps I have included the Console log from on of my attempts to syc.
Any ideas? Thanks for your time and effort in helping.
Jan 9 16:49:23 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 16:49:53: --- last message repeated 1 time ---
Jan 9 16:49:57 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 16:55:03 Rolf-Lufts-MacBook-Pro kernel[0]: 0 0 AppleUSBCDC: start - initDevice failed
Jan 9 16:55:03 Rolf-Lufts-MacBook-Pro kernel[0]: USBMSC Identifier (non-unique): 57442D574D41565530363531313730 0x1058 0x1003 0x175
Jan 9 16:55:23 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 16:55:53: --- last message repeated 1 time ---
Jan 9 16:55:56 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 16:56:26: --- last message repeated 2 times ---
Jan 9 16:56:52 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 16:57:26 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 16:57:56: --- last message repeated 1 time ---
Jan 9 16:57:56 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 16:59:07 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 16:59:15 Rolf-Lufts-MacBook-Pro kernel[0]: IOSurface: buffer allocation size is zero
Jan 9 16:59:39: --- last message repeated 4 times ---
Jan 9 16:59:39 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 17:00:23 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 17:00:53: --- last message repeated 1 time ---
Jan 9 17:01:23 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 17:06:40 Rolf-Lufts-MacBook-Pro kernel[0]: IOSurface: buffer allocation size is zero
Jan 9 17:14:34 Rolf-Lufts-MacBook-Pro kernel[0]: IOSurface: buffer allocation size is zero
Jan 9 17:17:18: --- last message repeated 3 times ---
Jan 9 17:17:18 Rolf-Lufts-MacBook-Pro kernel[0]: IOSurface: buffer allocation size is zero
Jan 9 17:21:46 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 17:22:16: --- last message repeated 1 time ---
Jan 9 17:22:44 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 17:23:14: --- last message repeated 1 time ---
Jan 9 17:23:14 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 17:23:48 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 17:24:18: --- last message repeated 1 time ---
Jan 9 17:24:22 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 17:24:52: --- last message repeated 1 time ---
Jan 9 17:28:04 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 17:28:34: --- last message repeated 1 time ---
Jan 9 17:28:37 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 17:29:07: --- last message repeated 1 time ---
Jan 9 17:29:07 Rolf-Lufts-MacBook-Pro kernel[0]: IOSurface: buffer allocation size is zero
Jan 9 17:29:12 Rolf-Lufts-MacBook-Pro kernel[0]: disk1s3: I/O error.
Jan 9 17:29:42: --- last message repeated 1 time ---
Jan 9 17:30:06 Rolf-Lufts-MacBook-Pro kernel[0]: IOSurface: buffer allocation size is zero

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ITunes sync problem: file could not be read or written

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