You might have some luck with Birdsoft's Ulti-Planner. Pretty slick program, offering a lot of PIM functions in one program which has a fairly small footprint. It's not a plugin running on the Today screen, just a standalone program. But it ties into Outlook very neatly and should synch Journal entries just fine, I think. Sorry, but since Activesync doesn't ever allow me to synch any databases I can't tell you for sure. Just try it and see, I guess.
http://www.ultiplanner.com/