I'm pleased to report my first successful PocketPC-to-Google Calendar sync experience. I'm giving GooSync a SwampDrain score of +2. I'm also finding that when my wife generates an iCal invite I read via Gmail, Gmail provide a simple way to RSVP back to my wife's iCal. I simply click "yes" within the Gmail, and the confirmation somehow finds its way into both my Google Calendar and my desktop Outlook (and then into Pocket Outlook via regular sync), and sends my wife an email she can click on to tell her Mac iCal calendar that I've confirmed. (My Gmail, though, doesn't seem to keep a record of the email message it's sending to her. Is there a way to configure Gmail to show that record?)
Now I'm looking for a service that will sync only a few categories of events from Pocket Outlook to Google Calendar. Not sure if GooSync or its competitors can do this, or if the limitation is in Pocket Outlook itself.
But it's the most progress here at the Swamp in some time!