New iMac, now contacts and cals won't sync to iPod Touch

After migrating from a G4/Tiger to an iMac/Snow Leopard on Friday, I have experienced many keychain and permissions-related problems. I have been able to solve all except one. It involves iTunes not syncing Info (contacts, cals, etc). I have tried everything under the sun and still cannot make it work. I have compiled a detailed account of the problem with screen shots here:
http://bit.ly/7YmE4S
If anyone has ideas, please post. I have not been able to arrange a support call with apple yet because it keeps getting rejected and I am told to try again later.

I set up a new standard user to see if iSync problem was solved and it was. Remember, I could not open iSync AT ALL in my current user account. I erased my iPod and synced it with the new user and it worked. At that point, I got fully committed to transferring my files over to the new user instead of piddling with more solutions that might or might not work for this and a variety of other issues that came up during migration. (Nothing against your suggestion which I am sure is a very good one...I am just tired of jumping through hoops with no results at this point and thought a fresh start was in order.)
Anyway, all seems well now. The new user account seems to have cleared everything up except for the printing, but that is due to apple dropping appletalk support, so I will have to tackle that in a different way. Transferring my files to a new user was not as laborious as I thought because most apps have export/import. I am still looking for a way to change permission to large batches of files/folders that are nested. "Apply to enclosed items" does not do the trick.
Thanks again for the assistance.

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QuickTime 7.6.5
FairPlay 1.6.16
Apple Application Support 1.1.0
iPod Updater Library 9.0d11
CD Driver 2.2.0.1
CD Driver DLL 2.1.1.1
Apple Mobile Device 2.6.0.32
Apple Mobile Device Driver 1.45.0.0
Bonjour 1.0.6.2 (118.5)
iTunes Serial Number 3891DB9D4B046846
Current user is an administrator.
The current local date and time is 2010-02-07 12:07:24.
iTunes is not running in safe mode.
Video Display Information
NVIDIA GeForce 7300 LE
** External Plug-ins Information **
No external plug-ins installed.
** Network Connectivity Tests **
Network Adapter Information
Adapter Name: {72D7672C-F1B0-445F-A926-7768301472E2}
Description: Intel(R) 82566DC Gigabit Network Connection - Packet Scheduler Miniport
IP Address: 74.129.136.73
Subnet Mask: 255.255.224.0
Default Gateway: 74.129.128.1
DHCP Enabled: Yes
DHCP Server: 74.128.18.196
Lease Obtained: Sat Feb 06 23:47:18 2010
Lease Expires: Sun Feb 21 23:47:18 2010
DNS Servers: 74.128.17.114
74.128.17.114
74.128.19.102
Active Connection: LAN Connection
Connected: Yes
Online: Yes
Using Modem: No
Using LAN: Yes
Using Proxy: No
SSL 3.0 Support: Enabled
TLS 1.0 Support: Enabled
Firewall Information
Windows Firewall is on.
iTunes is enabled in Windows Firewall.
Connection attempt to Apple web site was successful.
Connection attempt to iTunes Store was successful.
Secure connection attempt to iTunes Store was successful.
Secure connection attempt to iPhone activation server was successful.
Last successful store access was 2010-02-07 11:34:02.
** CD/DVD Drive Tests **
LowerFilters: PxHelp20 (2.0.0.0), DRVMCDB (1.0.0.1), DLACDBHM (1.0.0.1),
UpperFilters: GEARAspiWDM (2.2.0.1),
D: TSSTcorp DVD+-RW TS-H653A, Rev D300
Drive is empty.
** iPod/iPhone Connectivity Tests **
iPodService 9.0.3.15 is currently running.
iTunesHelper 9.0.3.15 is currently running.
Apple Mobile Device service 2.50.39.0 is currently running.
Universal Serial Bus Controllers:
Intel(R) ICH8 Family USB Universal Host Controller - 2830. Device is working properly.
Intel(R) ICH8 Family USB Universal Host Controller - 2831. Device is working properly.
Intel(R) ICH8 Family USB Universal Host Controller - 2832. Device is working properly.
Intel(R) ICH8 Family USB Universal Host Controller - 2834. Device is working properly.
Intel(R) ICH8 Family USB Universal Host Controller - 2835. Device is working properly.
Intel(R) ICH8 Family USB2 Enhanced Host Controller - 2836. Device is working properly.
Intel(R) ICH8 Family USB2 Enhanced Host Controller - 283A. Device is working properly.
No FireWire (IEEE 1394) Host Controller found.
After I updated to iTunes 9.0.3.15 I tried to sync my iPod Touch. All went well until this error message popped up; "Some of the items in the iTunes Library, including "headstrong", were not copied to the iPod "Sam's iPod" because you are not authorized to play them on this computer." ok so I go and authorize it type in my PW and Apple ID correctly and get this error message!; "We could not complete your iTunes Store request. The file or directory is corrupt and unreadable. There was an error in the iTunes Store. Please Try Again later."
I run diagnostics and this is what I got and pass all the tests except for the CD in the drive, could anyone please help? It won't allow me to sync any apps to my iTouch and half of my purchased music.
Connected Device Information:
DiePod, iPod touch running firmware version 3.1.3
Serial Number: 1A922MAE201
** iPhone/iPod Touch Sync Tests **
Sync tests completed successfully.

Are you on a Mac? I found this [Type -36 error (I/O Errors (bummers)|http://support.apple.com/kb/HT2433]
This file is having difficulty while either reading from the drive or writing to the drive. The file
may have been improperly written data to the drive or the hard drive or disk may be damaged.
This is almost always indicative of a media error (hard error on the disk). Sometimes (rarely) it is transient.
Solutions: Try copying the file to another drive. Use a disk recovery software, such as Disk First Aid to examine the disk. You can try rebooting with all extensions off. Once in a while this will allow you to read the data. The file in question should be restored from a backup that was stored on a different disk. Regular backups can reduce the time to recover from this error.
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It seems that ever since the last upgrade to iTunes (8.1.1) my contacts and calendar won't sync.
I've tried all the steps in http://support.apple.com/kb/HT1692 up to and including uninstalling and reinstalling iTunes but, nothing has worked.
Any help would be appreciated.

The contacts and calendar do sync into another user account but _only some of the records_.
ZoneAlarm. And there is no difference whether it is running or not.
One odd thing:
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Contacts and Caendar won't sync - how to turn off "over the air" syncing?

I have an 2nd gen 8GB Touch, a Macbook and use iTunes 8.0.1. I do not have Wi-Fi at home. I also have a dot-Mac (or Mobile Me, I guess) account.
When I first got the Touch, I opted in the iTunes Info section to sync both calendar and contacts, and everything came over fine. However, all of that somehow disappeared, and no amount of re-syncing will help. Now, my Info tab indicates that my contacts and calendars are being synced with my iPod over the air - I do not have the option of checking any boxes there. I have tried every permutation of settings in the iPod, but this doesn't change anything. I also cannot find any helpful help screens anywhere (including on this forum, where I have already searched).
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BobF

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http://support.apple.com/kb/TS1672

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I somehow suspect this is not what you mean:
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Message was edited by: foodpro

- Have you tried a reset. Nothing is lost
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John

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The contacts and calendar do sync into another user account but _only some of the records_.
ZoneAlarm. And there is no difference whether it is running or not.
One odd thing:
In order to try to find which record(s) might be causing the problem I sorted my calendar on the "Date Created" field hoping to be able to go back in history and see exactly when things went wrong. Much to my surprise I found that the 13 most recent records did not sync to my iPhone. Then the next 2 did. Then the next 3 did not. Then 1 did. etc.

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If you have deleted your MM email account from your iPhone and you have synced your iPhone with iTunes since - the email account settings should no longer be included with your iPhone's backup.
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See here for Transferring from your Old PC to your New Mac...
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New iMac, now contacts and cals won't sync to iPod Touch

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