I'm not sure how your Outlook platform works with respect to where it stores your calendar data, but I use Lotus Notes and my Calendar data is stored on my mail server, not my local PC.
Therefore I can set my mail AND Calendar to sync via wireless connection. Now I can enter/change a calendar listing and in the matter of a few moments, both are sync'd.
The only things I can't get sync'd wirelessly are Addbook and Memo Pad (Notes Prsnl Jrnl).
Hope this is helpful