Sync to Outlook with Google Calendar Sync
I've suffered major headaches trying to sync all my calendars. I used the Microsoft Outlook calendar on my desktop computer at home, but since I wanted to be able to access my schedule from anywhere, I also kept a copy of it on Google Calendar. When I traveled, I'd import my Google Calendar data into my laptop's Outlook calendar so I could access it offline. This was not only annoying to maintain, but also quite error-prone. If I made updates on any of the copies of my calendar, I had to make sure to make those same exact changes to the other copies, too.
This was my life for a whole year before we started working on Google Calendar Sync, a 2-way synching application between Google Calendar and the calendar in Microsoft Outlook. I was probably the most excited person on the team when we started developing it, because now I can access my calendar at home or on my laptop, on Google Calendar or in Outlook.
We can attest it does seem to work, though (as with just about everything Google) it's still in beta.