To have better control over your categories, you should purchase the professional version of Chapura Pocket Mirror. It gives you a great deal of control over all aspects of your Hotsynch w/ Outlook.
As a Treo 300 user, I also have to warn you about using the Chapura key contacts. It is superior to any Palm address book that I've seen, but doesn't play well with the Treo phone features. I don't know if Chapura's new Key Suite fixes this.
I had spent a great deal of time configuring outlook and Chapura about a year ago, but I for the details, as I no longer use Outlook, having switched to Time Matters <http://www.timematters.com>.