For some time, I’ve tried to the get the perfect calendar setup to manage birthdays, anniversaries, holidays, etc and I finally sorted it out a few months ago. I had tried the Outlook Connector but preferred one way updating as I wanted the online calendar to be the master source.
The new Windows Live Calendar beta allows you to share your calendar as a public ICS. Just set up you calendar then go to Share then Share this calendar and finally Make your calendar public.
This can be easily read by Microsoft Outlook 2007 (or Vista’s Calendar). To do this, just add it as a shared calendar.
Finally, I use Nokia PC suite to sync it to my phone. In the Sync app go to Settings->Microsoft Outlook->Select Folders and specify Windows Live Calendar as the preferred calendar.
While it might seem a lot of layers, Outlook is merely a middle man so there’s not really that much to it.
