Official Google Blog: Google Calendar Sync:Hallelujah. Bad news for gSyncIt and SyncMyCal but this was really something only Google can make work.
...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. When I add an event to the Outlook calendar on my laptop, Google Calendar Sync syncs it to my Google Calendar -- and since I also have Google Calendar Sync running on my desktop, the event then syncs from Google Calendar to Outlook calendar on my desktop. All of my calendar views are always up to date, and I can choose whichever one I want to use....
I'll have a report on my experience soon -- I sync my aging Palm to Outlook at home. In particular I'll be curious to see if it works with Google Apps.
Update: I had events on my Google Apps calendar from prior experiments, so I cleaned them out prior to my first sync (reset calendar to new state). I also backed up my Outlook Calendar by copying it to a PST file, so if it gets messed up I'll just delete and restore. (Takes only a few seconds. This doesn't work on an Exchange account btw, but I don't use Exchange at home.)
Update: It does work with Google Apps. As of today it will only sync with the primary calendar for the account. So if you want to sync work and home and view them together, you need to sync work to one Google account and home to another. You could, for example, set up a Team Edition calendar for work, and a Gmail calendar for home. You can then share the two to provide an integrated view -- something I've wanted for years. Then you can see how well this maps to the iPhone calendar! Exchange/Outlook Calendar work is much trickier than at home, so I won't be messing with Exchange any time soon.
I ended up syncing over 1100 events in Outlook to the newly emptied Google Calendar.
Update 3/8/2008: There's a bit of trickiness in the configuration.
Update 5/8/2008: It mostly works, but there's some problem with all day events between Google Calendar, Outlook and my Palm. They end up turning from an "all day event" into a "24 hour event" then time-shifting an hour. The fix is probably to get rid of my all day events -- until my iPhone arrives.
Another problem is that the default install launches Google Calendar Sync for every user. The fix is simple. Find Google Calendar Sync in something like: 'C:\Documents and Settings\All Users\Start Menu\Programs\Startup'. Move it to something like 'C:\Documents and Settings\jfaughnan\Start Menu\Programs\Startup'.