I have the syncing going on with my main PC and my laptop and I ran into a few problems like you are having. How I got around them....
Go into Synchronize then click on the Configuration tab then click Configure sync... Make sure what you want to sync on that computer is all checked (and make sure Outlook is what is selected to sync with of course). Next click on Configure -> Advanced Settings then click on Conflict Resolution and:
a) If you want to sync from the 8100 to the computer choose "Handheld Wins"
b) If you want to sync from the computer to the 8100 choose "Microsoft Outlook Wins"
Then OK, OK, Synchronize tab, and click Synchronize Now.
Also you can go in a wipe Outlook clean and then choose "Handheld Wins" and it will copy the 8100, or if you wanted to wipe the 8100 choose Microsoft Outlook Wins" after you erase everything