Migration from Outlook 2003 (pc) to Entourage 2008

So I've been having really bad luck with trying to get my iPod Touch to sync with Entourage. I have my calendar and approx 1000+ contacts in Outlook right now. The calendar seemed to sync, but when I try to sync the contacts, Entourage adds them in, and then after each subsequent sync it deletes all of them or duplicates them. I would just use address book, but it seems really elementary and also doesn't seem to have categories like in Outlook.

Has anyone successfully done this?

I have a Windows Mobile 5 device and didn't have a problem. I updated my contacts in Outlook 2003 (PC) and then did my first sync with Entourage 2004 via Missing Sync and it uploaded everything. A few weeks later, I upgraded to Entourage 2008 without a hitch. I do understand that 2008 syncs a little differently than 2004, but it still works for me. (I realize none of this helps you at all.)

As a last resort, Little Machines makes a downloadable program called O2M (Outlook to Mac). It costs $10 and will do what you want. It will convert your Outlook contacts into a format that can be imported into Entourage. It will also import your emails if you wish.

I'm sure there is a way to do what you want, but it might be worth spending $10 to save a half a days aggravation of trying to figure it out.

Edit: Now that I think about it, this wouldn't solve your problem either if you are having trouble with subsequent syncs. (This is a completely useless post.)