CoryB, does the Touch sync your calendar with the windows calendar when you sync it with iTunes?
It's kind of a work-around, but this is what I do:
I have installed
Google Calendar Sync. It constantly syncs your Google calendar with your Outlook calendar (you can set it to specific intervals). I have mine set to 2-way, so changes to my Outlook reflect on Google Calendar and the other way around as well. When I sync my iPhone in iTunes, any changes I've made on the iPhone calendar are pushed out to Outlook, and then pushed out to Google Calendar. Also anything changed on Google Calendar is pulled down and put into Outlook, and then into my iPhone. After initial setup, there is no thinking involved. The only drawback is that it is not an instant update, as syncing is required. Hell, I don't even really use my Google Calendar as much as I'd like to.
I'm running Vista, and I think there is a "Windows Calendar" that talks to Outlook behind the scenes. I never open Outlook, but it still makes the transfer between the iPhone and Google Calendar.