You posted this a while ago, so hopefully you see this.
I have Motorola Q9c which runs Windows Mobile 6.1. I sync it to a desktop (Vista) and a laptop (XP Pro).
From the standpoint of Outlook, you need to make sure that you duplicate the categories on both machines as you create new ones. Two seconds of extra work per new category..no big deal.
The problem I have, though, is that the syncing process does not work. The sync relationships keep breaking between my phone and the PCs.
And, if I update a task on one PC, the older version on the other PC overwrites the changes. So, I can't update my task list anymore and still sync to two PCs. I think there is a big flaw in Windows Mobile.