Cannot sync Calendar to new iPhone: OutlookSyncClient.exe error

Question

Hello. I just got my 4GB iPhone yesterday and started experiencing Calendar synchronization problems immediately. Everything else syncs fine, just not the calendar. The error I get is:
"OutlookSyncClient.exe has encountered a problem and needs to close. We are sorry for the inconvenience."
I have researched and have already uninstalled iTunes, Quicktime, and Apple related software, ran a registry cleaner, made sure all iTunes folders (except playlist and music folder) were gone and reinstalled. No luck there.
I have also uninstalled Office 2007 and all Apple related software, reinstalled, no luck either.
My PC is as follows:
HP Pavilion m7650n
Windows XP Media Center Edition with SP2
Intel Core Duo 2
1.86Ghz
2GB memory
360GB hard drive
My iPhone has the latest update of 1.0.1 and I am running iTunes version 7.3.2.6, which I downloaded off of the Apple website this morning.
My calendar is a critical part of my life, I work full-time, constantly scheduling appointments with customers, and I do work on the side, so I really need this to work.
I am a PC technician so I am comfortable editing and manipulating my PC, so any and all suggestions are welcome!

Answer 1

I would suggest doing a PST swap to see if that helps. These are the instructions I typed up, but I use Outlooks 2003. Since you are tech savvy, you can figure them out for 2007.
Troubleshooting Outlook Sync Problems
Many iPhone users have reported problems syncing with Outlook 2003 and XP (and other versions), and the reinstall of applications is not helping. Based on what I have read and my own experience, I have a theory.
My theory is that old recurring events, possibly created in an older version of Outlook and that you've had for a while, are causing the problem. It could also be new recurring events with weird recurrences (like the 4th weekday of every month). In any case, my money is on recurring events and some sort of corruption in the PST file that iTunes is simply not handling gracefully.
Here is a simple test you can try.
Find the Outlook PST file that contains all your data.
In Outlook 2003, click on File / Data File Management. That will display where your Post Office (PST) file is. Click on "Open Folder" to open a Windows Explorer window showing the file. Then, close Outlook.
Rename the file. This will make Outlook not be able to find it. Then restart Outlook.
Outlook will complain it cannot find the file, and open a browse window asking you to find it. Don't. Just create a new one by typing a name (like temp) in the Create/Open Personal Files windows, and hit enter. This will prompt you to create a new file. At this point, simply hit OK. Outlook may quit, so restart it again.
This will start Outlook with a brand new PST file. Now create a couple of sample contacts and calendar events, and sync.
Does it work?
My guess is that it will. This could prove the sync process works, and that iTunes just doesn't like your PST file.
Next step is to go back to File / Data File Management and open the folder where your PST files are. Close Outlook and delete your temp file. Make a COPY of the original file. This is important, because working with a copy will ensure you have a backup you can go back to in case something gets messed up. Then restart Outlook.
Since you deleted the temp PST file, Outlook will again complain it can't find the file, and ask for you to create or open one. This time, rather than create a new one, open the COPY of the PST file you made.
Now, change the calendar view by clicking on View / Arrange By / Current View / Recurring Appointments. Select all the recurring appointments and delete them. Try to sync again.
Does it work? My guess is that it will. This will prove that a recurring appointment was causing the problem. You can try deleting just the yearly recurring appointments first, which I suspect are the culprit, but you can test different combinations if you like.
If none of this works, you can always delete all temp and copies of PST files and reopen your original one. You will be no worse off than when you started, but this at least gives you a chance to troubleshoot the problem. Good luck!