Contacts not copying or deleting

I thought I had figured out the sync in the contacts, pref>contacts, click on the sync etc.. it seemed to work, however, I did two things, updated Itunes to version 6, then cleaned up my contacts in Outlook, now I only have A-D in the contacts the rest are gone. It says it's syncing but it don't. I deleted the .vcf file and re-sync'd nothing. I deleted the .vcf without syncing and the contacts are still there they did not delete.
So the mystery is
how do I delete contacts now that they are on the IPOD?
how do I get this to work besides manually? is there a delete all contacts button some where?
3rd, I've seen dicussion abouit updating IPOD software? did they mean ITunes or is there something I need to update on the IPOD? if so how?
Thanks
Jess

I have only had my iPod a couple of weeks, and tried to put my contacts from Outlook on it a few days ago - but they were not all copied across - there are some missing - I can't see anything in common with those that are not on my iPod; it just seems random.
I have also recently updated my Outlook Contacts, and when the iPod is updating I get a message saying that the contacts can't be updated - any ideas how I can overcome this?

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