For a while now, I've been looking for a good way to sync the calendar on my Macbook to Google Calendar to my Outlook at work. It'd be nice to be able to know what my next day at work looks like in Outlook, then to have my Calendar sync'd down to my laptop so that I can see and adjust things while offline, then sync it all back to the master calendar in Google Calendar.
It shouldn't be that tough, but so far, it has proven elusive. I've tried some of the free tools that are around to sync iCal with Google Calendar and Outlook with Google Calendar, but they've all proved a bit wonky.
Finally, Scoble mentioned that Plaxo had it's new beta that would do all of the syncing through a nifty web application. So, I headed over to Plaxo.com and tried it out. It seems pretty straight-forward. You add "sync points", which are places that Plaxo will sync your data to. I added Google Calendar, my Mac, and my work Outlook. The latter two required the installation of some software. Nothing too difficult. A couple of config tweaks later and I saw my work calendar in my Google Calendar and sync'd down to my Mac.
Except, over the following few days, I would constantly get duplicate calendars, lose the original calendar, get duplicate entries, continually have to tell Outlook which calendars I really wanted, which it would ignore and keep syncing other ones.
It became a royal mess.
So, I decided to uninstall things, get back to square one, and at least retain my Google Calendar the way it was. Except Plaxo ate my two calendars (because they no longer existed in Outlook ... lesson: kill your sync points before killing your calendars). That kinda pissed me off. Thankfully, my Mac still had my calendar, so I was able to dump the ICS entries and upload them to Google (import of ICS files is a nice feature of Google Calendar, by the way!). I lost my music calendar, but it was mostly older stuff at this point, so I started that one over.
Plaxo just didn't work for me, though it seems like it could be useful if they work the kinks out. It didn't sync to Google Calendar fast enough, which was always a bit annoying. The apps for the Mac and PC were kind of clunky, but they worked ok. But borking the calendar syncing was just a bit too much to deal with at this point.
So, I'm back to just subscribing to my Google Calendar feeds through iCal. I'm going to try gSync for about the 4th time and hope that the final release version is finally good enough to maybe think about using full time.
It'd be cool if Google solved this problem themselves (maybe opening up the GCal API), but I'm not holding my breath.