ITunes needs to close - Sync Outlook contacts or calendar

Question

I installed iTunes 7 after purchasing iPod. Everything works ok but if I select to sync contacts or calendar using Outlook (Outlook2003SP2) a error message appears: "itunes has encountered a problem and needs to close" - Error signature:
AppName: itunes.exe AppVer: 7.0.0.70 ModName: unknown
ModVer: 0.0.0.0 Offset: 35f7ddc9
After closing iTunes I restart it again and some seconds later the same error message appears. I have to deselect the "sync" option and everything returns ok but I could not have my contacts or calendar on iPod.
I saw a FAQ page explaining how can I export the contacts or appointments (as files) but I would like to know why this "sync" option doesn't work before do this "workaroud".
Any ideas that could help me solving this problem?
Thank you in advance!

Answer 1

This is the best remedy on the web for getting MANY contacts to sync from Outlook to your iPod.
First of all, you need to open iTunes and connect your iPod to make sure that you have enabled your iPod as a storage device. TO do this just look for your iPod in the DEVICES and select it. Summary Tab  Check the box, “Enable disk use.” Then make sure you click, “Apply” in the lower right corner.
In Outlook, go to Contacts and select all the items you want. You can use shift-click and control-click to choose multiple items. Choose Actions > Forward as vCard. This creates a new e-mail message with all the Contacts you selected converted to vCard format. Address and send the e-mail to a trusted friend - like yourself. Although all the vCards are right there for the taking, there's apparently no way to access them all at once except as a received e-mail. Collect your e-mail in Outlook. When you look at the received message, you should see all the vCards as attachments. Select the message that you sent with all the vCards. Choose File > Save Attachments > All Attachments. Note: if you use an e-mail program other than Outlook to collect your mail, it might not have the Save All Attachments feature. In the Save All Attachments dialog that appears, click OK. Next, you'll see a Save All Attachments file list. Navigate to your iPod's contacts folder. (Do NOT go to the folder called “iPod” in your program files. You need to find the name of your iPod in the various drives you have in your computer.) I didn’t name the folder. I just clicked OK and everything worked perfectly. You're done - the contacts have been shipped off to your iPod. Then I performed a sync and now I have every contact listed perfectly.
I modified the directions from http://findarticles.com/p/articles/mizd2969/is_200408/ain7183943
These are the best directions on the web because they avoid the individual vCard sync process.