I'm not much help either, but I know that DH tears his hair out trying to sync his iPhone with Outlook, and he is having to look for a replacement because apparently Microsoft is doing away with the software that allows the link?

One of the reasons I didn't get an iPhone was that before I got a smartphone, I was using an iPod Touch as my PDA, and tearing my hair out trying to sync it with Entourage (the old Mac equivalent of Outlook). Every time it would sync, it would duplicate recurring events.

I eventually had to abandon Entourage altogether and do everything in iCal, which is pretty bare bones, but it works, and that's the most important thing. I still miss ACT!...